Getting investors to yes.

Hard-won lessons from a serial fintech founder who has raised over $1B, the systems you need to always be fundraise-ready, subtracting > adding tools, and founder events you won't want to miss.

Welcome to The Startup Stack - where we cut through the noise to bring you the real talk, tactical tools, and startup trends that matter. This week, we're diving deep into fundraising mastery, cutting tool sprawl, and how AI is reshaping design and project management.

Featuring:

• Fundraising is like dating—except you can’t break up
• Streamlining investor comms
• Combatting the challenge of app sprawl
• July's must-attend events

The stack’s ready. Let’s get to work.

“Fundraising with venture capital is a transaction, but it's based on trust and reputation and belief. So it's a transaction that starts a relationship, whether you like it or not.” - Sasha Orloff , Co-Founder & CEO, Puzzle 🧩🚀

Sasha Orloff , serial fintech founder and CEO of Puzzle 🧩🚀 , joins Anastasia Crew , Notion ’s Global Startup Lead, to share hard-won lessons from raising over $1B across multiple ventures—and how modern founders can build faster, fundraise smarter, and stay ahead in the AI era.

Three fundraising cheat codes from Sasha:

• Fundraise from a position of strength—not desperation
• Use systems to stay fundraise-ready, always
• Pick investors like co-founders—you can’t break up later

Watch the full episode →

Fundraising Template: stay fundraise-ready with a centralized hub

• Streamline investor comms with messaging, CRM, and board updates all in one place.
• Arm investors with context through market research, TAM analysis, and more
• Make diligence easy with teasers, financials, and tailored data rooms

Get fundraise ready now →

"The average company uses 112 apps—yet work feels more fragmented than it did even just a few years ago.” - Statista, 2025

How many tools does your company use?

Most teams have a tool stack problem: they’re drowning in a sea of disconnected apps. Jumping between tools to search for documents, losing focus with constant context-switching, and duplicating work are symptoms of information fragmentation and tool sprawl.

And by no means are we immune to the sprawl virus at Notion. To ease our own pain, we started to:

• think about subtracting rather than adding tools
• use our own platform to solve it from within
• eliminate the cognitive overhead of maintaining multiple systems in parallel

Read how we're tackling software sprawl—and how you can do the same →

Mark your calendar - Notion for Startups is hitting the road.

Join us for bold ideas, lively conversations, and access to founders you'll want to meet.

• July 15 | San Francisco: First Block Live - From Thiel Fellow to $2B Startup: Inside Mercor. Invite-only taping of First Block with Brendan Foody, Co-founder of Mercor that leapt from dorm-room idea to a $2B valuation in just two years. | Request to Join
• July 17 | San Francisco: Designing with Intelligence: AI in Web Building. Hear from design leaders at Notion , Cursor , and Anthropic as they share how AI is reshaping how we design, build, and ship. | RSVP
• July 23 | Virtually: The Founder’s Toolkit. Get an insider look at how top tools like HubSpot , Carta , Brex , and others power startups to scale faster and smarter. | RSVP

The AI workspace that works for you. Startups move fast - and Notion helps you move faster. From idea to exit, build docs, manage projects, and run your team and startup in one connected workspace powered by Notion AI. Apply now to get up to 6 months of Notion’s Business plan with Notion AI included - a $12,000 value.

Until next week—keep turning ambition into action!