Lessons in Tenacity from Dennis Crowley, Co-Founder of Foursquare

Take this concrete step: your plan should be tied to what people actually do and tempered by fast experiments. Dennis Crowley co-founded Foursquare in 2009 with Naveen Selvadurai to turn simple check-ins into practical signals for local discovery. The early product offered tips and badges, and around a thousand venues joined in the first months. They proved that real value comes from how users meet them–the places they want to visit–rather than from hype alone. They wanted to build tools that merchants connect with nearby customers.

That path shows how tenacity shows up in daily work. Crowley built a culture where data explains the why behind each decision rather than guesses. He kept the team focused on one problem at a time and met user feedback with calm, even when numbers looked tight. Notable shifts emerged as the product split into two apps, Swarm for check-ins and Foursquare for city guides, a move that broadened the audience without losing core meaning.

Many teams chase rapid fame; Crowley tied the day-to-day work to a longer line of practice built over years. He kept the team focused on hard problems toward a dependable product. Personally, he says the core signal comes from talking with people who actually use the service. He wouldnt settle for vanity metrics and kept feedback loops tight.

Building this platform was not a cake walk; teams had to align around a shared cadence and rigorous testing. Notable milestones include the split into Swarm and Foursquare, a move that sharpened focus on check-ins and discovery while keeping data quality high and growth steady.

before you scale, apply these moves: tie a single user task to a narrow test, gather data, and explain what changed. Meet customers often, share a bright, concrete briefing, and pivot only when the evidence points that way. With many small experiments, you can turn initial momentum into lasting progress, and build resilience around you.

In short, tenacity means staying close to users, keeping a tight feedback loop, and turning principle into practice. Crowley’s path shows that a small team can affect many people over years, if you keep a calm tempo and learn from every misstep. wouldnt you apply those ideas to your next project?

From Dennis Crowley to California and Stanford GSB: Practical lessons in tenacity

Begin with a concrete 90-day MVP plan you can test locally, then target a move to California to tap into vibrant startup clusters. If youre a student with a belief in your idea, dreaming of impact, document each moment that confirms or challenges it; keep notes near your desk and use them to sharpen your pitch for investors. Since every setback hardens resolve, treat work as a craft you improve daily, not a single push.

Culture shapes tenacity. Humility keeps you grounded; you carry it into each thought and conversation. When you hear a comment or a note, you give attention and apply it. The star you aim for is not a badge but the steady progress you learned from peers and mentors. The world rewards clear listening and practical action, not bravado.

Keep a seed mindset: plant small bets, test quickly, and iterate. Favor conversations with investors who demand clarity. Every turn becomes proof of progress; your first labels for your product set the tone, and your chin stays up in hard rooms. When moving into new markets, listen to voices in the industry and adapt your approach.

From Dennis Crowley’s California step to Stanford GSB engagement, the practical lesson is to treat every encounter as a test of tenacity: show up early, keep notes, and translate learning into execution. In California, you map a path that connects user need with sustained effort. In Stanford GSB, you convert that discipline into peer critique and sharp decision-making.

To apply these lessons today, build a simple 12-week plan: 1) define your 90-day test, 2) line up mentors in California, 3) craft a clear set of milestones that demonstrate traction, 4) document results so you can share a compelling story with investors. Believe in the process, stay moving, and know that weve built momentum with every moment you invest.

Identify a precise user need and validate it with a simple, trackable metric

Name a single, real user need named by your initial market conversations and validate it with a simple metric you can track over a week. Pick one core action that proves value and design a minimal experiment around it. If you found early signals, you can move much faster; though the path may feel difficult, this focus keeps the team moving.

Whats the smallest action that proves the need and can be tracked in seven days? Frame it as activation: what share of new users perform the core action within the week? Label each cohort, tell the story to the board, and speak plainly about what the numbers imply, though they are early and imperfect.

Set up a seed prototype that addresses the need with minimal features. Use easy instrumentation and track a single metric: activation within seven days. Run the test with 50–100 users from the market, keeping the scope small so you can learn quickly. Keep labels simple and map actions to products so you can tell an interesting story to stakeholders about potential scale.

Read the results as a clear signal for the path ahead: if activation hovers around 20–25% and first-week retention is solid, the market likely supports a profitable product and you can move toward scale. If the metric stays under 10%, certainly reconsider the need or pivot. This approach helps businesses decide what to fund and what to drop. Also, look for a rosy uptick in the data that suggests momentum.

Dennis Crowley showed the tenacity to turn a tiny seed into something the board could trust. He spoke with users, told the data story, and brought wilson into the conversation to align on next steps. He turned early signals into a real product by refining labels and the user flow, sold the idea to the team, and kept moving, like many founders.

To apply this yourself, pick a named need, run a week-long seed test, and tell yourself to keep it simple and easy. Track the metric, tell the people who sold you the idea, and speak to the board with labels and a clear path to scale. This process helps me, myself, and the team stay focused on what actually moves the market and turns ideas into products. This is not about ever making bigger bets, but about learning.

Ship a lean MVP to collect real-user feedback and iterate fast

Ship a lean MVP with a single core feature that delivers value in under 10 days to collect real-user feedback and iterate fast.

This will become easier as you focus on a single problem. Dreaming about a full product isn’t necessary; you must ship a tiny prototype and learn quickly. Keep the scope tight and validate the riskiest assumption before expanding.

Define a narrow audience and cant trust a broad sample. Both early adopters and power users can contribute, but you should test with one clear group first. A compact plan helps you move faster and learn without getting stuck in thinking about every edge case.

Build a minimal version that actually worked in practice for other teams. Avoid bloating the flow; include only what proves value and what you can measure. If something didn’t perform, iterate on the core interaction rather than overhauling the entire UI.

Instrument minimally: in-app prompts, a short three-question survey, and optional 15-minute interviews. Capture a comment and, when users tell you which part mattered most, theyd told us that the simplest path often holds the answer. They may share tough trade-offs, but you can learn from them and adjust quickly. Theyll see that you listen, which fuels future engagement.

News from early users helps you decide next steps and keeps the team aligned. Over years of developing products, teams played with dozens of approaches; this lean path grows the chance of a successful outcome while avoiding wasted effort. The aim is to learn fast, then ship the next single improvement that moves metrics in a meaningful direction.

Frame setbacks as experiments with timeboxed iterations and guardrails

Start by treating every setback as a testable hypothesis and lock a timebox of 5–14 days to learn something concrete. This creates momentum, reduces debates, and lets youre move forward with data instead of opinions. In crowleys moments, setbacks signal what to test next and you identify the next experiment quickly, like a musician fine‑tuning a track until the rhythm feels right.

1. Frame the setback as a precise hypothesis. Write one sentence: If we change X for users in Y condition, then Z outcome will occur. This keeps the team focused and makes it solvable within the timebox.

2. Timebox with guardrails. Set a period of 5, 7, or 14 days depending on complexity, and declare a preplanned stop date. If you reach the guardrail thresholds, you pause or pivot; if not, you proceed to the next step.

3. Define guardrails clearly. Budget cap, risk threshold for negative user impact, and a decision gate (continue, pivot, or kill) because those boundaries keep the effort accountable and reduce the gamble.

4. Choose concrete metrics. Use a leading indicator (activation or engagement within the first 3–7 days) and a trailing indicator (retention after 14 days). Mark the experiment as solved when the hypothesis meets its criteria or is decisively disproven.

5. Regular, short talks and updates. Schedule quick talks every periods to share findings, and send a concise email with the learnings. This creates a single source of truth and keeps the union of teams aligned.

6. Document and create a reusable learnings memo. Capture what worked, what didn’t, and why. A simple template helps teams reuse insights across launches and protect culture from silos.

7. Maintain humility and openness. Talk openly about failures, acknowledge what you solved, and invite input from diverse voices because that culture grows stronger when people feel safe to voice concerns.

8. Decide next steps and advance. If the hypothesis is validated, launch the next iteration; if not, adjust the X variable and run another timeboxed test–again and again–until you identify a viable option to move forward.

Example scenario: you want to raise onboarding activation from 14% to 22%. Frame the hypothesis, timebox 10 days, set guardrails (max spend $2k, no negative NPS impact beyond -5), track activation and 7‑day retention, and document the outcome in an email to the team. If activation hits 21% within the period, you proceed to launch; if not, you test alternative copy or a shorter onboarding flow. This approach mirrors how crowleys teams identified the next test after each launch, turning setbacks into a steady stream of experiments that fuel forward momentum, not fear, and keep the culture grounded in humility and evidence.

With this method, music and momentum align; you take down barriers to learning, reduce risk, and create a repeatable pattern that every period helps businesses grow. The option to advance remains clear, because each learning cycle delivers data that informs the next decision, and the organization moves forward with intention, not hesitation.

Tap the Bay Area ecosystem and Stanford GSB networks for mentorship and resources

Reach out to crowleys-aligned mentors in the Bay Area and Stanford GSB alumni who run weekly mentoring circles; this union delivers quick feedback, access to executives, and concrete resources that does accelerate a startup’s next moves, with thrilling, practical insights.

Next, map out who to talk to: executives with track records in scaling, product leads who critique prototypes, and founders who have navigated tough funding cycles while building. Look for places where these groups converge, then sent your intro notes with a tight one-pager to unlock bigger opportunities than before, through coaching andor advisory tracks.

Talking with dozens of mentors, theyd said that different programs fit your startup’s culture and growth stage across periods; the next turns often include 15-minute chats, then longer sessions, and mentors wanted to see real progress, which can unlock millions in value.

Finally, implement a weekly rhythm: sent intros to 5-7 mentors, track responses, and schedule 3-4 pilot conversations. If you went through a Bay Area network, you would see faster feedback and bigger chances for collaboration. Another useful habit is documenting what works and what doesn’t, which compounds over time.

Build repeatable processes and a team culture that sustains grit through growth

Define a razor plan and lock it into a weekly cadence: decisions logged, owners named, outcomes dated, and risks pushed down to the owners for action. This razor clarity feeds speed and reduces confusion when markets shift, so youve got a stable baseline to push from, and you can stay sure about the path.

Pair the plan with a living playbook: a 2-page decision log, a simple post-mortem template, and a quarterly health check on team confidence. Capture what changed, why it happened, and what helped the team adapt next. Include a steady haul of metrics so the team can see not only output but the effect on customers; avoid duplicative steps; each item has a single owner and a ready-to-share note. We wrote a short memo to capture the rationale behind the changes.

Build a culture that invites voices from every corner: engineers, designers, artists, marketers, and public customers. A dedicated learning board surfaces perception and recurring learnings, while every contribution gets a clear signal back to their contributor. This reduces silos and supports growing teams to stay aligned without creating extra meetings. Look for signals in behavior and outcomes to verify that every voice shaped decisions. I remind myself that feedback is fuel. The working rhythm stays visible in simple dashboards.

Keep updates visible to investors and the public through concise notes and simple dashboards. We wrote concise notes that investors can scan and look for next-turn signals; share progress on twitter and with the team, highlighting a thrilling, notable win and the reasoning behind each turning point. When signals are sent publicly, trust grows; when signals stay internal, teams move faster.

Next steps to scale culture: empower managers to keep the cadence, train new leaders on the process, and codify exception paths. Document how decisions survive turnover and how new hires accelerate grit. youve got to measure engagement and adjust the approach; comment with feedback and assign it to owners. In this world, a predictable routine beats chaos.