GM Logo
Gagan  Maheshwari
2 emails a month

Payments and fintech, explained like an operator.

Short notes for CEOs, CPOs, and product leaders building payments platforms, modernizing systems, and applying AI to ship faster with measurable outcomes.

70+ executive and product workshops and roadshows
Led and shipped high-impact engagements across payments, risk/compliance, platform modernization, developer tooling, and AI launch readiness
Checkout and activation work tied to 700K+ net new actives and improved NPS

Unsubscribe any time.

Gagan Maheshwari

Who this is for

CEOs, CPOs, and product leaders

  • You’re scaling a regulated platform and need velocity without chaos.
  • You want an operating model that aligns product, engineering, risk, and legal.

Payments, risk, and ops leaders

  • You want modernization without breaking audit trails or controls.
  • You’re tired of pilots that die in review, rollout, or incident response.

Boards, PE, and VC operators

  • You need clear signal on platform health and execution.
  • You want a simple way to stress-test modernization and AI plans.

What you will get

Frameworks you can reuse

Decision templates for portfolio bets, platform sequencing, and what’s “safe to ship” in payments flows.

Patterns from the field

What actually breaks in onboarding, payments, disputes, risk, and platform modernization, and how strong teams respond.

Exec-level translation

Clear language for boards and leadership teams: tradeoffs, governance, metrics, and outcomes.

Start here

A few notes that match the tone.

Agentic AI guardrails that actually ship

How to make autonomy safe in regulated systems: least privilege tools, policy vetoes, human gates, auditability, evals, and circuit breakers.

Read

How I think about scaling regulated platforms

My operating philosophy for bridging enterprise reliability and startup velocity—without breaking trust.

Read

Browse all insights

If you want the full archive.

Read

FAQ

How often do you send it?

Two to four emails a month.

Is this technical?

Written for exec and product leaders. Some systems detail when it matters. No ML theory.

Is this only about AI?

No. It’s mostly platform scale, operating model, and payments reality. AI shows up when it materially changes outcomes, and when appropriate controls can be defined.

Can I unsubscribe?

Yes. One click.

Do you sell or share my email?

No.

Join the list

If you’re scaling a payments product, this will save you time and help you make better calls under constraint.

Two to four emails a month. Unsubscribe any time.