Digvijay Singh Shekhawat

Chapter I — D2C / YC Attempt: A Fast Lesson in Consumer Reality

My first serious attempt was in D2C, built with the YC mindset:

ship fast, test aggressively, and aim for immediate traction.

The consumer market corrected that optimism quickly.

What became clear:

  • Margins are unforgiving.
  • Differentiation disappears fast.
  • Distribution > product quality.
  • Attention is rented, not owned.
  • “Interesting” is not the same as “useful.”

It was a good technical and creative exercise, but a poor business.

It forced me to understand how emotion drives consumer behavior and how brittle “virality” actually is.

Key takeaways:

  • Consumer logic is emotional, not rational.
  • Speed helps survival, not scale.
  • Without distribution, even great ideas stall.

This phase gave me pattern recognition, not success — and that’s fine.

It taught me to respect markets that don’t care about effort.


Chapter II — B2B SaaS: ₹60 Cr and the Discipline of Enterprise

Moving from D2C to enterprise SaaS was a shift from chaos to structure.

Here, we grew a product to ₹60 Cr+ in revenue, and the learning curve was very different.

What enterprise actually rewards:

  • Reliability over novelty
  • Trust over theatrics
  • Process over improvisation
  • Risk reduction over “innovation”
  • Predictability over speed

I learned how SLAs, procurement cycles, compliance, and integrations shape product decisions.

And how enterprise buying committees make choices: slowly, rationally, and based on perceived risk.

Key takeaways:

  • Execution compounds; noise doesn’t.
  • Enterprise value comes from removing anxiety.
  • You don’t scale features — you scale systems.

This phase built my operational discipline and long-term thinking.

It taught me how durable companies operate.


Chapter III — Bootstrapping AI: Focus, Constraints, and Real Signals

Building my own AI company after that was a different experience altogether — lean, quiet, and very direct.

No funding story.

No theatre.

Just building, selling, iterating.

What bootstrapping forces:

  • You build only what someone will pay for.
  • You ship fast because you have to.
  • You validate through revenue, not applause.
  • Every decision has an immediate cost.
  • Cash flow replaces narrative.

It strips away all illusion.

You learn what actually matters in a product and what is just noise.

Key takeaways:

  • Constraints sharpen judgment.
  • Independence sharpens clarity.
  • The work forces you to grow up fast.

This stage turned me from someone who builds products into someone who builds a business.


Epilogue — Putting It Together

Each phase contributed something essential:

  • D2C taught me how consumers think and why distribution matters.
  • B2B SaaS taught me operational discipline and scalable systems.
  • Bootstrapping AI taught me clarity, focus, and real proof of value.

Together they form the foundation of how I approach design, product, and strategy today — not as theory, but as accumulated operating experience.

Simple. Direct. No theatrics.

I. Luck: The Hidden Element

Luck isn’t randomness — it’s biased toward people who are already moving.

Fortune favours the prepared, the positioned, and the perceptive. To attract luck, orient toward environments that generate options, cultivate sensitivity to weak signals, and keep capabilities primed. Luck is not mystical; it’s the reward for active preparedness.

Takeaway: Position + perceive + act.


II. The Game of Growth

Cognitive growth requires novelty and challenge. Avoid the comfort of mastery by repeatedly choosing domains where you’re bad enough to learn but not so lost that you stop. Cycle across domains — competence, then a new friction — and you keep plasticity alive.

Takeaway: Growth = intentional incompetence.


III. The Beginning of the End

Every project starts as a fragment. Pain and friction are informative signals, not punishments. Value lies in the forward motion — in iterating, learning, and starting again. Endpoints are illusions; the real state is continuous becoming.

Takeaway: Treat struggle as fuel.


IV. The Product Cycle

Products are relationships. They must be usable, useful, findable, credible, and desirable. Track their lifecycle (Adoption → Habit → Personalization → Plateau → Abandonment) and intervene with features, messaging, or pivots to renew relevance.

Takeaway: Design for lifespan, not launch.


V. Holacracy: A New Way to Lead

Distribute authority through clear roles and processes. Replace permission-seeking with process-backed autonomy so people act confidently without bottlenecks. Leadership becomes orchestration, not command.

Takeaway: Structure + autonomy = agility.


VI. The Information Hunt

People forage for information with evolved heuristics. Build interfaces that match those heuristics: predictable scent trails, clear affordances, and minimal cost for exploration. Design that mirrors human search behavior feels effortless.

Takeaway: Align product flows with human instincts.


VII. Heckel’s Law: Value Over Visuals

If perceived value is high, UI polish matters less. Solve a real problem first; then refine. Beauty amplifies, but value retains.

Takeaway: Solve the core job-to-be-done before you optimize aesthetics.


VIII. Tools: The Art of Effortless Action

Great tools minimize friction and cognitive load so users can act without thinking. Predictability, forgiving defaults, and clear outcomes make tools feel like extensions of intent.

Takeaway: Make the tool invisible.


IX. Appropriation: The Unplanned Life of Products

Users will invent uses you didn’t plan for. Those emergent behaviors are product gold — they expand markets and reveal latent value. Observe, enable, and sometimes institutionalize them.

Takeaway: Design for affordances, not just use-cases.


X. Disposition & Emotion in Design

Experience comes from a triad: disposition (mood), cognition (processing), and design (input). Respect context and nudge toward positive states. Reducing frustration is often more valuable than adding delight.

Takeaway: Design for mood as much as mechanism.


XI. Usability: Respect for Humanity

Usability is ethical. It’s about respecting time, attention, and cognitive resources. Measure effectiveness, efficiency, and satisfaction in real contexts — then iterate.

Takeaway: Usability is a moral stance.


XII. Complex Systems: Beyond the Components

Systems reveal properties their parts don’t. Anticipate interaction effects, feedback loops, and emergent behavior. Intervene at leverage points, not just components.

Takeaway: Map interactions before optimizing parts.


XIII. The Duality of Science & Art in UX

UX lives between rigor and resonance. Research gives you the map; craft gives you the poetry. The best products harmonize both.

Takeaway: Use evidence to inform aesthetics.


XIV. Processes: There Is No Single Right Way

Frameworks are scaffolding, not scripture. Diverge to explore, converge to commit. Use pragmatic blends that suit context.

Takeaway: Process is a tool, not a value.


XV. Conclusion: Design as a Philosophy

Design shapes decisions, identity, and behavior. Good design helps people achieve what they intend; great design shifts what they imagine possible.

Takeaway: Design is practice and persuasion.


XVI. Decision-Making Under Uncertainty

Most impactful choices happen with incomplete data. Use probabilistic thinking, set priors, and update often. Prefer reversible experiments to irreversible bets. Explicitly state assumptions and the conditions under which you’ll pivot.

Takeaway: Treat decisions as experiments; optimize for optionality.


XVII. Ethics & Responsibility in AI

Power requires stewardship. When building AI systems, center harm-minimization, auditability, and human-in-the-loop controls. Transparency builds trust; safety constraints limit short-term gains but enable long-term adoption.

Takeaway: Ethical design is product-market fit for the future.


XVIII. Feedback Loops & Metrics

Measure what shapes behaviour. Identify leading indicators, not just lagging metrics. Instrument early, iterate constantly, and beware vanity metrics that mask decay.

Takeaway: Metrics should inform action, not justify past choices.


XIX. Radical Empathy & User Research

Empathy is discovery, not projection. Spend disproportionate time with edge-case users; they reveal constraints everyone faces. Ask less about solutions and more about stories: “What were you trying to do?” builds clarity.

Takeaway: Observe problems before inventing solutions.


XX. Time, Attention & the Economy of Focus

Attention is finite. Design features that respect session length, reduce context-switching, and minimize interruptions. Encourage deep work for teams by protecting focus blocks and asynchronous communication.

Takeaway: Design for sustained attention, not maximal engagement.


XXI. Hiring, Culture & Onboarding

Hire for judgment, curiosity, and culture-add (not culture-fit). Onboarding is a product: teach principles, not processes. Early hires should scale decision-making, not just execution capacity.

Takeaway: Hire for leverage and teach autonomy.


XXII. Resilience, Failure & Iteration

Failure is data. Normalize quick, cheap failures and extract learning rapidly. Build recovery systems: post-mortems that assume systemic causes, not individual blame.

Takeaway: Fail fast, learn faster, ship forward.


XXIII. Experimentation & Hypothesis-driven Design

Run small, high-quality experiments. State hypothesis, metric, and minimum viable test. Treat A/B tests as conversation starters, not final answers.

Takeaway: Test assumptions before scaling.


XXIV. Storytelling & Narrative in Product

Stories give context to features. Use narrative to orient users: what they can do, why it matters, and what success looks like. A clear story reduces friction and aligns teams.

Takeaway: Translate features into user stories.


XXV. Scalability & Systems Thinking

Scale isn’t just more of the same; it requires rethinking constraints. Identify which components must be robust and which can remain fragile early. Plan for graceful degradation and multi-tier resilience.

Takeaway: Scale the right parts, not everything.


XXVI. Craftsmanship & the Maker’s Mindset

Ship with care. Small details compound into trust. Balance speed with discipline: tests, reviews, and deliberate refactors preserve momentum over years.

Takeaway: Respect craft; it compounds credibility.


XXVII. Founder Wellbeing & Sustainable Pace

You are the system’s thermostat. Burnout reduces leverage — make recovery non-negotiable. Build routines that protect cognitive bandwidth: sleep, exercise, reflection, and deep work. Delegate ruthlessly.

Takeaway: Sustainable founders build sustainable companies.


XXVIII. The Long View: Compounding Advantage

Small, consistent choices compound. Culture, user trust, and technical debt accrue slowly — in both good and bad directions. Choose the direction you can live with for decades.

Takeaway: Optimize for 10+ year effects.