How2 Decide Which Bets Are Worth Taking
Turn your risky ideas into smart, calculated moves without gambling your startup away.
Why Thinking in “Bets” Beats Guesswork
Every founder makes bets.
Hiring someone new.
Launching a new feature.
Entering a new market.
Running a big marketing push.
The problem is, most founders don’t think of these as bets. They treat them as inevitable “next steps,” when in reality, every move carries uncertainty and some are far riskier than others.
Thinking in bets changes the game. Instead of asking:
“Should we do this?”
You ask:
“Is this a bet worth placing right now?”
This shift helps you prioritise, de-risk, and recover faster when things don’t work out.
Step 1 – Define Your Bet Clearly
A bet isn’t just “build a mobile app”, that’s too vague.
Instead:
“Bet: Building a mobile app will increase our daily active users by 30% in the next 6 months.”
Why it matters:
You know exactly what you’re hoping to get.
You can measure success.
You can revisit the bet later to see if it paid off.
Step 2 – Map the Assumptions Behind It
Every bet rests on a stack of assumptions. If the wrong one crumbles, the whole thing falls apart.
Four common assumption types:
Problem – Do customers actually face the pain we think they do?
Solution – Will our idea solve that pain effectively?
Market – Is the timing and demand right? Are competitors doing something similar?
Behaviour – Will people actually do what we want them to (sign up, pay, share)?
Example:
Bet – “Launching a referral program will increase sign-ups by 20% in 3 months.”
Problem: People want to refer friends.
Solution: Our referral reward is motivating enough.
Market: No competitor is already offering a better incentive.
Behaviour: People will actually share the referral link.
Step 3 – Score the Risks
For each assumption, rate:
Impact if wrong (low, medium, high)
Likelihood it’s wrong (low, medium, high)
Anything with high impact + high likelihood is your make-or-break risk. That’s the part you need to test or address first.
Step 4 – Decide if the Bet is Worth Placing
Before you go all-in, ask:
Is it cheap or expensive in time/money?
Can we test cheaply before full commitment?
Do we have capacity to recover if it fails?
Does it align with our current priorities?
If you can’t afford to lose this bet right now, shelve it until you can.
Step 5 – Place Small Bets First
The smartest founders don’t go all-in immediately. They place small bets to de-risk bigger ones.
Example:
Instead of building a full mobile app, run a landing page ad campaign to measure demand for mobile features.
This lets you keep your downside low while keeping upside potential high.
Pro tip: Think like a poker player. You don’t have to win every hand … you just need your winning bets to more than cover your losses.
Bringing It All Together
Thinking in bets:
Makes risk visible.
Forces you to test your riskiest assumptions first.
Helps you avoid sinking months into dead ends.
Want a ready-made way to do this?
Our How2 Assumption & Risk Mapping Template walks you through identifying, scoring, and prioritising bets and deciding which to take now, later, or never. (drop us a mail to receive our latest version)
If you’d rather have a guide, our Bets Workshop helps teams learn how to map and de-risk their biggest plays for the quarter in a single session.