What I Learned Working With 100+ Startups
After 13 years and over a hundred clients, these are the patterns that separate the winners from everyone else.
A few months ago, I realized I’d crossed a milestone: over 100 startups worked with across 13 years. Some became unicorns. Some shut down within a year. Most landed somewhere in between.
Looking back at all of them, certain patterns emerged—things that had nothing to do with the product, the market, or even the team’s talent. These are the lessons I keep coming back to.
The Founders Who Win Think in Systems
The best founders I’ve worked with don’t chase tactics. They build systems.
“We don’t have a marketing problem. We have a learning velocity problem. Every week we’re not shipping experiments, we’re falling behind.”
— CEO of a dev tools company (now valued at $800M+)
That mindset shift—from “what should we do?” to “how do we learn faster?”—is the single biggest predictor of success I’ve seen.
The Five Patterns That Matter Most
After analyzing what worked across all these companies, five patterns stood out:
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Speed of iteration beats quality of strategy. The startups that won weren’t smarter—they were faster. They’d run three experiments while competitors were still debating which one to try.
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Distribution is harder than product. Almost every founder underestimates this. Building something people want is table stakes. Getting it in front of them is the real game.
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Culture compounds. Early hiring decisions echo for years. The first 10 people set the DNA. Choose carefully.
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Cash efficiency creates options. The companies that survived downturns weren’t necessarily the best-funded—they were the most efficient.
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Storytelling is a force multiplier. The founders who could articulate their vision clearly—to investors, to customers, to candidates—had an unfair advantage at every stage.
What Failed Startups Had in Common
The failures taught me as much as the successes. Here’s what I saw repeatedly:
- Premature scaling. Hiring aggressively before finding product-market fit. Every time.
- Founder conflict. Technical disagreements are solvable. Values misalignment is fatal.
- Ignoring unit economics. “We’ll figure out monetization later” is a death sentence.
- Building in isolation. No customer conversations. No feedback loops. Just building.
- Copying playbooks. What worked for Slack won’t work for you. Context matters.
The Questions I Now Ask Every Founder
When I start working with a new company, I ask the same questions:
About the Business
- What’s your current CAC and LTV? (If they don’t know, that’s telling.)
- Where do your best customers come from organically?
- What would break if you 10x’d growth tomorrow?
About the Team
- Who’s your first call when something goes wrong?
- What decision are you most uncertain about right now?
- When was the last time you changed your mind about something important?
About the Market
- Who’s your real competition? (Hint: it’s often “doing nothing”)
- What’s changing in your market that creates an opening?
- Why now? Why didn’t this exist five years ago?
The answers reveal more than any pitch deck.
The Advice I Wish I’d Gotten Earlier
If I could go back and tell myself one thing at the start of this journey:
“The best work happens when you stop trying to be impressive and start trying to be useful.”
That applies to consulting, to marketing, to building products. Usefulness compounds. Impressiveness fades.
Key Takeaways
If you only remember five things, make them these:
- Systems thinking: Weekly experiments and documented learnings.
- Distribution focus: At least half your effort goes to getting in front of the right customers.
- Culture intentionality: Written values that are actively used in hiring decisions.
- Cash efficiency: Operate with 18+ months of runway whenever possible.
- Clear storytelling: One sentence that makes people lean in and want to hear more.
If you’re building something and want to talk through where you are, reach out. After 100+ startups, pattern recognition is the most valuable thing I can offer.