Small Bets: The Smarter Way to Create, Build, and Succeed

How creators and solopreneurs turn uncertainty into opportunity through experimentation

If you're an indie hacker or a Micro SaaS founder building with your own savings, you know how uncertain everything feels. Every line of code feels costly, and every big feature launch feels like a gamble. Sitting at your desk, staring at your product dashboard. No users yet. You've spent months building and you're still not sure if anyone will care.

That's the problem with big bets.

Forget *starting a company. *Just try making $1,000 with a small project first.

That mindset shift can save you months of wasted effort and anxiety.

The truth is, even in large, sophisticated product teams, success is rare. 95% of new products fail make no measurable impact (source). Success is unpredictable, which means relying on a single "big bet" is like gambling your future.

The antidote is to change how you approach risk and creativity itself.

That's where the idea of Small Bets popularised by Peter Sims in his book Little Bets and Daniel Vassallo through his community Smallbets comes in.

What Are "Little Bets"?

Peter Sims describes little bets as:

Concrete actions taken to discover, test, and develop ideas through the acceptance of affordable loss.

In simple terms, it's about learning by doing taking small, low-risk steps that generate insight and open new directions. Sims studied world-class innovators like Steve Jobs, Pixar's Ed Catmull, comedian Chris Rock, and architect Frank Gehry.

What they all shared was a willingness to start small, experiment, and adjust rather than chase a perfect big idea from the start.

Every creative breakthrough be it an iPhone, a hit comedy routine, or a Pixar movie starts with messy, uncertain experiments. Great ideas emerge, they aren't born perfect.

The Small Bets Mindset

Ex-Amazon engineer Daniel Vassallo brought this idea to small-time entrepreneurs.

His philosophy: rather than betting everything on one startup idea, create a portfolio of small, low-risk projects things you can launch quickly, learn from, and, if needed, abandon without pain.

He puts it simply:

A good idea is an idea that doesn't break you if it doesn't work.

Each project is a bet a reversible experiment. Some will fail quietly, a few will pay off, and over time, your odds of success compound.

Vassallo likens this to building optionality the same way investors hold multiple options, you hold multiple creative possibilities by not putting all your eggs in one basket.

From Pixar to Prototypes: Embrace Imperfection

Pixar, a company celebrated for creative excellence, embodies this philosophy.

As Ed Catmull said, "All our movies suck at first." Every film begins as a crude storyboard, gets torn apart, reworked, and rebuilt dozens of times before it shines.

That's what Sims calls "experimental discovery."

The process of learning through small, imperfect steps rather than chasing big, flawless ideas.

Similarly, as novelist Anne Lamott reminds us, every good piece of writing begins with "really, really shitty first drafts." The courage to start messy is what unlocks innovation.

Design for Affordable Failure

Whether you're an artist or a founder, failure is your tuition fee but it should be affordable.

Both Sims and Vassallo emphasize designing your process so that no single failure can break you.

Spend weeks, not months, on early versions.
Invest only what you can afford to lose.
Focus on experiments that produce learning, not validation.

This approach keeps you resilient, nimble, and in motion.

Stop Seeking Validation, Start Seeking Insight

In the startup world, we glorify "validation." But validation implies certainty and there is no certainty in creativity or business.

Vassallo learned this the hard way. His product Userbase had thousands on a waitlist, hit the #1 spot on Product Hunt when it launched, and early revenue yet it still failed to gain traction, costing him $100,000.

The lesson? Data doesn't equal destiny.

Instead of looking for validation, look for signals hints of interest, early engagement, small wins. These are breadcrumbs that tell you where to go next.

Sims echoes this in Little Bets: innovators succeed not by planning for success but by discovering it through iteration and feedback.

Borrowing from Hedge Funds: Bet Small, Bet Often

The world's most successful hedge fund, Renaissance Technologies, doesn't make giant bets. It wins through thousands of small, low-risk trades each with a slight statistical edge. Over time, those tiny edges compound into massive returns.

As a creator or indie hacker, you can apply this same principle:

Treat every experiment as a micro-trade.

A new pricing model, a UI tweak, or a new marketing channel all are small bets.
Size your bet to your confidence.

Use the Kelly Criterion mindset: scale investment with your evidence, not your ego.

The goal isn't to be right once, it's to stay in the game long enough for small wins to snowball.

Pricing as a Small Bet

When you ship a new product, think of pricing as another experiment.

Contrary to popular belief, sometimes upfront payments outperform subscriptions.

A one-time fee can trigger impulse purchases because customers feel ownership.

If your average lifetime value (LTV) is $180, why not charge $180 upfront? It's the same amount, but simpler to sell.

Early on, underpricing slightly can be strategic it helps you gain users, feedback, and word of mouth. Later, as confidence builds, adjust pricing for new customers only.

Each change is a data point, not a commitment.

Find Your Inspiration Generator

If you want to keep making small bets, you need a constant flow of ideas a system for inspiration.

For Daniel Vassallo, it's Twitter, where random threads spark new project ideas.

For others, it might be Reddit, podcasts, YouTube rabbit holes, or scanning expired domains! (as Peter Askew does).

The goal is to stay curious and exposed to randomness.

Good ideas rarely come from isolation; they emerge from seeing patterns others miss.

Payoff of Small Bets

When you place small bets:

You reduce fear.
You learn faster.
You stay adaptable.

Over time, those small, compounding discoveries build a career, not just a company.

Forget the grand vision for now.

Start with one small, affordable experiment.

Then, place your next bet.