Big bets, Small Bets
When to bet big, when to play it steady, and how to know the difference in your product strategy.
👋 Hey, Sam here! Welcome back to The Product Trench. Every other Wednesday, I cut through the noise to share actionable insights, no-nonsense advice, and stories related to product management and leadership.
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I once bet my entire product roadmap on building a revolutionary analytics & insights feature using business accounting data that would "change everything" for our startup. Six months and countless coffees later, we launched to crickets. Meanwhile, our competitor shipped three new data integrations and stole 10% of our customers, including an enterprise one.
Ouch.
That expensive lesson taught me something crucial about product strategy: betting isn't about going all-in or folding. It's about knowing when to make calculated risks versus steady plays.
The betting mindset
Sometimes, I think product strategy is like approaching a tough CrossFit workout.
Do you stick with the exercises you know you can manage, keep a steady pace, and get it done without too much fuss? Or do you go all-in, tackle the heavier weights, risk hitting failure, but potentially set a new personal best? It's a choice between the comfort of what's achievable and the thrill (and risk) of a breakthrough. In product terms, this is the story of big bets versus small bets—the constant balancing act that every product leader faces.
And right now, many of us are looking at the year ahead, trying to figure out how to tackle these challenges in a way that's both steady and ambitious. We're the ones making the call, and the outcomes can be uncertain.
Moonshots and roofshots
A big bet is a moonshot—the type of project that gets people talking, maybe even redefining your company. Think of launching the first iPhone or Netflix's move to streaming. A small bet, on the other hand, is more like adding another topping to a well-loved pizza—it's not revolutionizing anything, but it keeps people coming back for more.
Big bets are intoxicating. They're why many of us got into product in the first place—to make something that has an impact, to change the game. But let's face it, they're risky. A big bet that doesn't pay off can leave your team tired, your resources drained, and your users still wanting more of the basics they asked for.
Small bets are the unsung heroes. They're your bug fixes, your minor usability tweaks, and those small features that quietly make everything smoother. They're not going to land you a TED Talk, but they build trust, keep users happy, and make sure the ship stays afloat.
The truth is, you need both. The need for both moonshots and roofshots isn't just theoretical—how you balance them depends largely on your company's unique position. Only moonshots, and you'll lose the foundation that makes big bets possible. Only incremental improvements, and you'll never break out from the pack. The key is understanding when to lean into which—and for that, context is everything.
Betting Differently
Depending on where your company is in its lifecycle, the way you balance these bets will look different.
Startups
You're scrappy, you're hustling, and every resource counts. It's tempting to swing for the fences and make the big bet that puts you on the map. But in these early stages, a lot of your value comes from showing your users that you're listening—that you're there to make their experience better week by week. This means small bets matter. Sure, take a moonshot or two—they're often why people buy into startups—but don't ignore the quick wins that can turn your early adopters into evangelists.
At my previous startup, Corl, we bet on a new feature we thought would redefine our value. It got some buzz, but what actually retained users were the smaller bets—things like speeding up our onboarding flow and fixing key bugs our first customers hated.
Scale-ups
You're past the survival stage. Now, it's about finding your place and protecting it. Competitors are nipping at your heels, and users have expectations that can't be ignored. Here, you've got to balance the immediate customer needs—roofshots—with strategic bets that show you're thinking about where the market is headed. Maybe that's a new feature that feels a bit bold, but just might be what secures your space in a shifting landscape. The art here is defending your territory while pushing the boundaries.
At Rails, we faced intense competition. We made a big bet on analytics & insights to differentiate our product, but our growth also depended on those small bets—constantly iterating on user-requested features and reducing friction to keep our existing users happy while we pursued bigger visions.
Digital transformation
Legacy companies undergoing digital transformation have a different challenge. Often, it's less about proving value and more about reimagining it. A pure moonshot approach can be dangerous—you can't forget the fundamentals of why your existing customers stick around. Yet, sticking purely to small, cautious steps can mean missing out on the real, transformative shift you need to stay relevant. Here, the bet mix is about stabilizing your digital presence while also signalling that the company is moving forward, not just surviving.
In my consulting days, I worked with a few "legacy" companies undergoing digital transformation. With one particular client, we had to ensure their existing users weren't alienated. While we made a big bet on an entirely new digital experience, small improvements—like adding more user-friendly features (things like dark mode) to their traditional interface—ensured their core audience didn't feel left behind during the change.
Practical takeaways for evaluating your bets
So, how do you make sure you're balancing things right? Here are a few prompts that might help as you sit down to plan:
Look back to look forward
Are there bets you made last year that didn't pan out, not because they were wrong, but because the timing was off? Revisiting old bets with fresh eyes can sometimes be the key to unlocking new value.
Check the bet mix
Is your team burned out from chasing too many big ideas, or are they bored from focusing on the mundane? Do you have the capacity to execute? Healthy teams need variety. The best bet mix keeps people challenged without exhausting them.
Assess market shifts
Are new players entering your space with bold moves? Are your metrics showing slower growth? Sometimes, stagnation is a signal that it's time for a bigger swing. Conversely, when things feel a bit chaotic internally, it's time to focus inward and stabilize before the next big push.
Final thoughts... and a reality check
Here's the uncomfortable truth: most of us aren't going to create the next iPhone. And that's okay. The real skill is in knowing which bets to make and when.
I've seen too many product leaders and founders fall into what I call the "TechCrunch Trap" - chasing headline-worthy moonshots while their core product slowly becomes irrelevant.
Sometimes, the best bet is the boring one. My team once spent two weeks fixing API documentation bugs instead of building our planned analytics suite. That "small bet" reduced customer success escalations by 38% and, over time, boosted time to value. Not exactly TechCrunch material, but it paid the bills.
Remember: Every Netflix started with a good DVD delivery service. Every iPhone began with a well-executed iPod. The art is in knowing when to maintain your roof and when to shoot for the moon.
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— Sam ✌️