Hey everyone,
Happy Sunday from Arizona.
It’s awesome to be here with the best of the best for Money2020 – the top fintech conference of the year.
One of my portcos, Baselayer, is nominated for Startup of the Year. LFG.
Most people think they know how to sniff a win. They actually don’t.
If you misdiagnose a win, you waste quarters.
If you do it twice in a row, you could lose your company.
If you truly can’t sniff a win as a startup operator, you’re dead.
This is one of the most critical skills to learn.
The team needs to feel where the momentum is hiding and move toward it with little hesitation.
Moving fast looks different depending on the company.
Path A: Build a durable, high-quality product → then pour fuel on sales.
Path B: Build a scrappy MVP → sell → shape the product in real time.
With Path B, you get signal early, trade perfection for feedback, and iterate (and mess up) in public.
The key is directional accuracy under uncertainty.
Founders who take longer to find their wedge often compensate with extreme acceleration and a killer product once they do.
Rilla is a perfect case study: years of exploration, followed by a four-year run from $0 to $50M+ ARR
Other times, teams build a scrappy MVP, see if there’s any PMF, and iterate on the product.
Consumer products mostly fall into this category (example: CalAI), but tools like Lovable and Cursor will certainly accelerate this for B2B.
When you’re building from zero, you don’t have time, you don’t have capital, and you don’t have a wide margin for error. If you’re pushing on the wrong lever, you’re done.
Here’s exactly how to sniff a win:
Identify the core growth lever you need to move
Wins are murky at first – you need to know what stat sig looks like
Make sure you have revenue, retention and PMF
Identify the Core Growth Lever: Always Revenue
The “win” you’re sniffing needs to tie back to revenue. It’s okay if that’s not an A (product) -> B (revenue) equation, but you still need to be able to map it back.
Example: At Citizen, our 40M automated email sends a year to resurrected users, and a % of these converted to paid subscription tiers = $$.
The win should focus on how to increase revenue.
Sometimes, the win is hidden in the below places:
Trait | Why it matters | What fake wins look like |
Revenue adjacency | It leads to monetization soon or predictably later | “Brand awareness,” “community,” “engagement” with no downstream capture |
Compounding | Each cycle gets cheaper or more powerful | One-off stunt you can’t replicate |
Distribution built-in | It pulls more users in as it works | You need marketing to drag traffic to it manually |
Measurable movement | You can see the system bending toward $$ | It feels exciting, but it doesn’t move a real KPI |
This can be either by retention, resurrection, or new rev streams.
Ask these four questions to see if what you think is a win could actually be a win:
If this works, does money show up?
Does this reduce CAC, increase LTV, or unlock a new pay path?
Will this scale cheaper over time? (compounding > force)
If we turned off all marketing, would it still drive revenue?
Once you’re grounded in the fundamentals, your advantage comes from spotting the thing that’s working
How to See Through the Murk
The operators who win are the ones who can interpret behavior before the charts scream it.
You need to know your metrics like the back of your hand.
Behavior of new users:
What is the buying behavior of your new users?
What features do they try first?
Example: If you get a cohort of new users based on marketing that talks about a new feature, do those cohorts use that new feature in their first session?
What does this type of excitement look like in the product (example: usage per key surface area is up 2X in the first week)
Behavior of buyers for each feature:
At what point in the user journey do they buy or activate certain features?
Is this tied to what your sales team is selling as core functionality?
What additional features do they start to upsell to as they get deeper into your product?
Retention and what spikes it
What is the top feature that retains users?
What levers can you pull from winning features that retain users to new features you’re shipping?
Do you want to overlap the user journeys together?
Although this sometimes this may be outside of features too, like brand, customer service, speed, your features MUST be naturally retentive or else you don’t have PMF
Behavior of champions and how they use your product
What do your champions care most about?
When they make moves in your product and encourage downstream usage inside an org, what features see the most spike?
What does this look like for revenue?
What external marketing motions can you build to mimic and multiply champion behavior? (example: external emails using champion testimonials)
The 3 Holy Grails
Focus on these 3 pillars when sniffing a win.
To create a truly successful product, you need all 3. But to sniff a win, you can look at these areas individually.
Retention: Do people even stick around?
If you have a sticky product + people are aware of it = retention
Top teams review retention by customer segment, acquisition channel, and product feature, constantly asking: “Are people coming back for the same value (or are we doing something new/better, + is retention holding up as we grow?”
How do different cohorts behave? Did you ship a new feature, onboarding, or product marketing lever that boosts retention?
Recurring signals = plateauing retention curves (users stick after initial drop-off), increasing repeat purchase frequency, or increasing engagement with new product releases
Revenue: Is this making you $$?
Building features isn’t free. It costs employee burn + time + eng resources.
Because revenue is dissected by source, cohort, and moment of conversion, you need to know if this potential win is driving it.
What product actions or events tie directly to paying moments: adoption, trial-to-paid conversion, upgrades, renewals, upsells, and resurrection?
If the win you’re sniffing is doing any of the following, follow it:
MRR goes up
ARPU goes up
LTV increases
CAC decreases
Product Market Fit (PMF)
Product-market fit happens when customers return (sticky), pay (revenue), and tell others about your product (organic growth) = drives natural pull to you and growth momentum.
Ways you can measure PMF:
Retention Flattening: If your retention doesn’t drop off a cliff and the curve levels out (users stick after the early period), that’s a foundational PMF clue.
Product-Led Growth: More and more new users come in via referrals or organic word-of-mouth, not just paid channels. That’s the market pulling your product forward.
Talk to Users to Validate: User surveys (“How disappointed would you be if you couldn’t use this?” + aim for 40%+ answering “very disappointed”) and in-product NPS to double-check.
Well, How’d I Do:
Sniffing a win requires rigorous self-awareness about the product, obsessive curiosity about users, and disciplined, data-led decision making.
It is the top lever for you to separate traction before its 100% certain or kill a project because the metrics aren’t moving the way they need to.
The win will speak for itself in any of the data points outlined above, so its your job to not get clouded in decisions because of your “natural instincts” and “gut feelings” – that B.S. will keep you burning on the wrong builds instead of chasing gold.
Sniffing a win + knowing what to do next is one of the hardest, most critical jobs for any founder and operator.
When your product fits the market, it all compounds: momentum, revenue, retention, and brand/reputation.
I hope you have a productive week with a clear-eyed run toward your next big win.
Julia
