TLDR FOUNDERS 2026-02-20

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FUNDRAISING STARTS BEFORE YOU NEED CAPITAL

Most founders lose the fundraising game by waiting until they need money to start pitching. The real process begins with building an investor prospect list and seeking feedback rather than capital to establish early relationships. By sending monthly updates and executing publicly, founders create scarcity and FOMO, often securing commitments before a round even officially opens.

POWER IN THE AGE OF INTELLIGENCE

Tech companies like Stripe, SpaceX, and Base Power illustrate the "winner takes more" trend, where firms leverage technological advancements to dominate industries. The focus shifts from protecting software moats to identifying industry constraints, breaking them, and seizing "High Ground" for expansion. As technology progresses, companies controlling scarce assets benefit the most, driving increased economic concentration and growth opportunities.

THE SOFTWARE SHAKEOUT: WHAT IS DURABLE AND WHAT IS NOT IN THE AGE OF AI?

$1T in software market cap evaporated in three weeks. This framework sorts the survivors from the dead. Software in the path of doing work (CrowdStrike, Stripe, Shopify) is durable. Software that generates paperwork about work (DocuSign, Monday.com, Zendesk) gets replaced by AI that just does it. The scary middle - Atlassian, Salesforce, HubSpot - is eroding slowly but the cliff is coming. If you're building a product that humans fill out so other humans can read, rethink the entire premise before your next board meeting.

HIRING FOR A NEW ROLE/FUNCTION FOR YOUR FIRST TIME? DO THIS FIRST.

A bad first hire in a new function costs you a year. The fix takes one week. Before you write the JD, do 5-10 calibration calls with people who already hold the role at companies one stage ahead of yours. You'll learn what "great" actually looks like, what comp is real, and which interview questions actually separate the best from the mediocre. Most founders skip this step and end up hiring on vibes. Don't be that founder.

ADVICE WE REJECTED TO BECOME ONE OF THE FASTEST GROWING START-UPS EVER

Deel co-founder Shuooo Wang details how the company scaled by ignoring traditional startup "best practices," such as hiring a VP of Sales early or focusing on the SF talent pool. Instead, Deel prioritized founder-led sales to maintain customer context, hired for traits over pedigree, and invested in 100+ local entities to build a moat around compliance and reliability. By favoring frugality and vertical M&A over high burn, the company leveraged first-principles thinking to become one of the fastest-growing startups.

AGAINST “AGAINST TASTE”

Taste is informed judgment built through experience rather than passive curation. True taste is exercised during the creation process through invisible, compounded decisions that lead to elegance and coherence. While AI can generate outputs, humans remain the essential definers of quality, setting the standards and directions that tools cannot shortcut.

BOOST.SPACE

Single source of truth database for automations and AI agents.

LAYERS

AI marketing agents that analyze your product and run growth campaigns.

CONWAY

Autonomous AI agent infrastructure layer.

THERE IS NO PRODUCT

If you remove the difficulty, you remove the product. If it only takes a weekend to build a product, then anyone else could do it in a weekend, too. You can't just add features and hope the market comes back, because there's no core product. Some software will still be an asset, but most of it will become inventory, and every model generation will push that line further.

IN DEFENSE OF VERTICAL SOFTWARE

The industry is currently asking why vertical software needs to exist when AI companies are pouring billions of dollars into building the most powerful general-purpose AI systems in the world. Enterprise software is just code, but that's not where the value of software comes from. The value of enterprise software comes from understanding the process and the organization well enough to make the software do exactly the right thing. Process engineering will continue to be the foundational advantage or vertical software.

WHY CEOS' AI HYPE REALLY ISN'T LANDING WITH EMPLOYEES

Business leaders are struggling to translate AI enthusiasm into effective organizational change as employee skepticism grows.

THE SAAS RESET: WHY SAAS IS CHANGING, NOT GOING AWAY

The traditional build vs. buy equation has flipped as AI drastically reduces software creation costs.

THE BEST COMPANIES YOU'VE NEVER HEARD OF

A portfolio company went from zero to $30M+ run rate in two years.