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THE SILENT STARTUP KILLER

Sometimes a big board is your biggest liability.

WHY FIXING WEAKNESSES IS KILLING YOUR LEADERSHIP

WHAT HAPPENED TO MY TRAFFIC?

Chegg sued Google after losing millions of visitors to the new AI Overviews feature, which seems to deliver Chegg-like homework answers right on Google. Traffic dropped 34%, sparking the first lawsuit of its kind. Others are feeling the impact, too—Stack Overflow and HubSpot also saw steep dips, while The New York Times thrived, possibly thanks to a lucrative licensing deal. It's a sign that AI-driven search may transform how users discover content, and companies without special partnerships could watch their traffic fade.

VENTURE PSYCHOLOGY

Early-stage investing is more about the founder's grit than fancy projections. Investors look for relentless, problem-obsessed individuals who will pivot, iterate, and outwork everyone else. History shows that markets shift, products evolve, and competition pops up—what truly matters is whether the founder will quit or not. That unstoppable mindset, plus a willingness to adapt, often outweighs even the best-drafted business plan or pitch deck.

EARLY STAGE BRAND DESIGN

Don't overinvest in visual rebranding - focus on product and market fit instead. Early-stage startups should aim for a "good enough" brand design and avoid expensive and lengthy design projects. The key is building something that solves a problem and that people want.

MISTAKES IN DUE DILIGENCE THAT KILL DEALS

Loads of founders think a term sheet is the hard part—until investors start combing through the numbers. Sloppy financials, mismatched growth metrics, or a chaotic cap table can scare off potential backers. Failure to address legal snags, compliance issues, or fuzzy IP rights also sinks deals fast. Getting everything buttoned-up and transparent is often the difference between a successful close and a last-minute collapse.

AN OPERATOR'S GUIDE TO PRODUCT STRATEGY

Two complementary layers shape a great product roadmap: a near-term “small S” strategy to fix current issues, and a longer-term “big S” vision that imagines the product's future three to ten years out. Collecting user data, brainstorming, and building quick prototypes helps teams converge on realistic plans for now and aspirational plans for later. The key is to force disciplined choices about where you'll focus finite resources—and designing with both immediate and eventual goals in mind.

"STEALTH MODE" AND OTHER F'ING BRILLIANT STRATEGIES

Keep your startup in stealth mode to avoid early competition and distractions. Focus on perfecting your product before launch and don't worry about customer validation. Concentrate on coding and raising funds early while benchmarking against competitors without fearing differentiation.

COHERENCE

Synthetic ground truth data for AI applications.

PEPPR

Convert scattered knowledge from all your existing tools into an AI-powered, self-improving knowledge hub.

AGORA API (PRODUCT)

Agora API enables developers to search, purchase, and track orders for 10 million products sold on 25,000 Shopify and WooCommerce stores.

FIVE EMERGING VC SWIMLANES

The venture market is fracturing into distinct tiers: tiny pre-seed funds, inception-stage firms, new Series A specialists, mid-sized “too big but not big enough” players, and supersized billion-dollar platforms. Each swimlane has different fund sizes, risk appetites, and target exit multiples. Founders need to know which lane their potential investors occupy so they can raise capital from partners whose portfolio strategy—and check size—truly aligns with their startup's stage and ambitions.

THE IMPACT OF FOUNDER PERSONALITIES ON STARTUP SUCCESS

Research shows that startup founders' personality traits significantly impact their ventures' success. Specific Big Five traits like adventurousness and openness are more common in successful founders. Startups with diverse personality types among their founding teams have higher chances of success.

IS GROWTH STILL GOOD?

AI companies are reaching $40-80M in revenue faster than ever, with startups like Harvey hitting $50M ARR in just three years. However, rapid growth may actually signal vulnerability - without network effects or unique tech advantages, these companies are often finding "shallow gold" that competitors can easily replicate. Metrics that used to prove success now raise questions about defensibility in a market flooded with corporate innovation budgets.

JOE LONSDALE EXPLAINS THE “ONE THING” RULE HE LEARNED FROM PETER THIEL

Founders who chase too many revenue streams usually end up chasing their tails.

LONG-TERM SELFISH (AND THE CIRCLES OF US AND NOW)

Selfishness can be short-term—like a toddler scribbling on the couch—or it can be mature and long-term, taking into account the future and a wider circle of people.

HERE ARE THE TYPES OF AI COMPANIES ENTERPRISE VCS WANT TO BACK IN 2025

VCs are focusing on AI solutions for specific enterprise tasks, emphasizing application-focused companies that solve unique challenges.

HIRING JUDGEMENT

When it comes to leadership hires, gut instincts often matter more than you think. It's easy to get lost in candidate “scorecards,” but remember that a strong track record isn't enough. Leaders have to navigate unknowns, so you're betting on their judgment more than their resume. Pick people who thrive under uncertainty and can handle critical, high-stakes decisions in real time.

BENCHMARKS STRIPE, KLARNA, & THE FINTECH RESURGENCE

In fintech, revenue streams aren't created equal—here's why some startups soar. From Stripe's towering multiple to Klarna's comeback, valuations depend on the risk mix in your business model. Payments and stable SaaS can earn higher marks, while lending-heavy models face bigger swings. For founders, it's a reality check: recurring income drives higher valuation, so steering your startup toward predictable revenue can pay off.

THE ANATOMY OF A BREAKTHROUGH “SERVICE-AS-A-SOFTWARE” BUSINESS

Chargeflow's unique success-based pricing model fueled rapid growth, attracting 15,000 merchants and recovering millions in chargebacks. By investing in GTM strategies before product development, Chargeflow improved customer acquisition and retention. Its approach, focusing on seamless onboarding and value demonstration, differentiated it in marketplaces like Shopify and Stripe.

RAISING CAPITAL IN A TOUGH MARKET

Even healthy metrics can face skepticism these days—here's how to push through. Investors are more cautious than ever, so you'll need a crystal-clear story that shows why your market matters, what your metrics really mean, and how AI fits (if at all). They're also more likely to trust founders who tap warm introductions from existing backers. Bottom line: if you combine evidence of strong fundamentals with a compelling vision, you stand a better chance of securing funding despite a tough climate.

FINDING NEW WAYS TO RE-INVENT YOURSELF

Question your own success so you don't block your next breakthrough. Inspired by how Apple dared to shift from iPods to iPhones, this read encourages founders to disrupt what's already working. Sometimes you need to “destroy” familiar tactics or product lines to open doors to bigger, more impactful innovations. If you feel stuck optimizing the same wins, it's a push to challenge the status quo and embrace what's next.

THE SURPRISING PATTERNS BEHIND VIRAL AI PRODUCTS A DEEP DIVE INTO BOLT, CURSOR, GRANOLA, PHOTOROOM, REPLIT, AND MORE

Kintsugi. Get started

EMOJIS

AI Graphic Designer for SMBs (starting with AI emojis).

CONTRARIO

AI Matchmaker for recruiting 10x engineers.

CROCT (PRODUCT)

Croct helps product teams scale UI optimization by offering built-in AB testing and personalization, ultra-low latency APIs, design system integration, and quick implementation.

EV STARTUPS KEEP DYING

Canoo's bankruptcy highlights the recurring pattern of EV startups collapsing despite high-profile partnerships. The company burned through funding while paying millions for executive perks like private jets, all while generating less than $1M in revenue. The piece examines how constant pivots - from subscription vehicles to commercial vans to military contracts - along with misplaced priorities on deals over operations, doomed the company. Canoo joins a growing graveyard of EV startups that couldn't survive the capital-intensive reality of automotive manufacturing.

THE FOUR PILLARS OF VENTURE INVESTING

Venture capital has four core jobs: finding deals, picking investments, winning deals, and supporting companies. The article shows how focusing too much on one area often means sacrificing others - like how being great at finding hot deals might make you worse at picking good investments. Through real industry examples, it explains why most VCs can't excel in all four areas and need to choose their strengths carefully.

THE PROBLEM WITH AI THAT'S TOO HUMAN

Just as early cars were designed to look like horse carriages, we're stuck thinking about AI in human terms. The article uses this historical parallel to show why our current AI applications might be too limited by human-like design.

THIS STARTUP IS SELLING FOR $1B, SO WHY IS ITS FOUNDER NOT PROUD OF THE OUTCOME?

Divvy Homes sold to Brookfield Properties for $1 billion, but due to debt obligations, common shareholders received no payout.

VENTURE FUNDS' MARKUPS STAGNATE & DISTRIBUTIONS UNDERWHELM AS STARTUPS REMAIN IN A CONTRACTION PERIOD

AngelList reports a stagnant TVPI for recent venture funds on its platform, with U.S. startups experiencing historically low investment activity in 2024.

A 10 POINT CHECKLIST TO USE WHEN YOU SELL YOUR COMPANY

David Frankel of Founder Collective created a checklist for navigating company acquisitions.

* New trends such as AI-driven pricing and outcome-based models

* 2025 pricing predictions and how to stay competitive

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THE LNO FRAMEWORK

The LNO Framework is a way to categorize your tasks into three buckets—Leverage (L), Necessary (N), and Optional (O)—to ensure you use your limited energy on the things that truly move the needle. Leverage tasks (L) are the high-impact work that directly advances your product or strategic objectives. Necessary tasks (N) are routine responsibilities you can't ignore—like approvals or maintenance—but don't spark huge outcomes. Optional tasks (O) are the ones you can drop without significant consequences.

WHEN IS A MARKET TOO SMALL FOR VCS?

“Too small a market” from a VC's mouth doesn't mean your startup is worthless. It means it's not big enough to yield the 10-100x returns they need. Venture math demands massive exits to power their portfolios, so a $500M outcome might be too small for some big funds. Thus, the lesson: find investors aligned with your realistic exit potential. If you're not aiming for multi-billion scale, micro-VCs or angels might fit you better rather than chasing top-tier funds that pass due to market size constraints.

TOGETHER AI ANNOUNCES $305M SERIES B

Together AI has announced a $305 million Series B funding round led by General Catalyst and Prosperity7, with participation from investors like NVIDIA and Salesforce Ventures. This investment will enhance Together AI's position as a leader in AI Cloud solutions, with a focus on supporting open-source AI models and NVIDIA Blackwell GPU deployment.

NON-OBVIOUS SEO ADVICE FOR STARTUPS

For early-stage software startups, it's easy to get stuck following surface-level SEO tips, but truly effective SEO means doing a few less obvious but powerful things: first, be defensive by creating content about direct comparisons and integrations so potential customers find your page instead of a competitor's. Second, focus on low-volume, high-intent keywords (like “Electron analytics”) that match specific user needs—hundreds of these niche terms add up quickly. Third, Google is largely “looking at the people,” i.e., user behavior, not just your content, so do everything possible to ensure visitors stay on your pages and like what they see.

HOW TO TELL A CONSISTENT STORY

This article introduces a framework: “perceptions,” a set of big-picture themes that unify your brand's narrative. Once defined—3 to 5 of them—use them to guide all campaigns and content so everything aligns. This process prevents random, disjointed marketing. It's practical because if your brand story is fuzzy or scattered, your audience tunes out. With perceptions as your North Star, you can quickly evaluate ideas for consistency, ensuring your marketing feels cohesive across channels.

GETTING PRESS FOR YOUR STARTUP

Cold-emailing journalists seldom works. They're bombarded by PR blasts all day. Instead, build relationships well before you need coverage: follow them, share their articles, and become a helpful source. Then pitch a real story that benefits their readers. It's crucial because real press coverage can spark new users, partners, and even investors, but only if you're delivering something truly newsworthy. By approaching it as a long-term game, you avoid that typical “spray and pray” approach that yields nothing.

BASEDASH (PRODUCT)

Basedash is an AI-native Business Intelligence platform that can create dashboards and instantly understand your customers using natural language.

NOWADAYS (PRODUCT)

Nowadays is an AI-powered event planning copilot that takes the hassle out of organizing corporate events.

SENSE (PRODUCT)

Sense uses AI to automatically organize related resources and updates across all apps for each project and person in your team.

6 HARD-WON LESSONS FROM SELLING MY STARTUP

A founder recounts the months-long grind to a 9-figure acquisition. The biggest takeaways: companies are “bought, not sold,” so keep building until you have leverage. Lawyers can drag things out for bigger fees, so it helps to push for a quick close. Also, watch out for how your employees fare in deal negotiations. Many founders dream of that big exit but are unprepared for the emotional whiplash, endless legal slog, and potential heartbreak. This piece highlights how to keep your company strong (and less distracted) until the wire hits.

HOW TO GROW ON TWITTER (2025 EDITION)

For startup founders feeling lost in the noisy world of social media, this guide shows that Twitter can be a surprisingly personal space for sharing your unique journey. It breaks down practical tips—from crafting hooks that grab attention to repurposing content that resonates—reminding us that real growth comes from connecting authentically with people who care about your story.

WHERE WILL THE AI HORDE STRIKE NEXT?

AI disruption isn't one big invasion; it's a wave of startups simultaneously probing every market niche, from Hollywood to social media. Legacy players can't just defend one fortress; there's always another angle for AI founders. AI's expansion is like a roving horde of nimble companies. You either partner up or risk being overrun—because the AI horde can adapt, pivot, and push wherever it sees weakness.

THE GIFT OF GRATITUDE

Teachers, mentors, and friends often shape our paths in powerful ways, yet we rarely take the time to thank them deeply or pay forward their kindness.