Founder Fridays No. 142
The Founders’ Emotional Gauntlet -- Is Your AI Idea Any Good? -- Stripe
Happy Friday.
The Founders’ Emotional Gauntlet
Startup culture glorifies the grind while underplaying the emotional tsunami that founders actually face — building both a company and your founder identity simultaneously in mid-air. Your impressive pitch deck won't save you from profound loneliness, identity crises, and the realization that achieving milestones rarely brings the relief you anticipated. Instead, prepare by identifying your specific fears (financial instability, judgment, co-founder conflict) and create proactive strategies like building financial runway, practicing rejection therapy and establishing non-negotiable, self-care boundaries before you need them. Remember that founder success requires building systems for resilience and cultivating multiple support circles — not just grinding harder when willpower inevitably fails. First Round Review (17 minutes)
Is Your AI Idea Any Good?
The artificial intelligence gold rush has founders rushing to launch startups, but success rarely hinges on the idea itself — it's all about execution. Rather than chasing what's trendy, apply this five-part stress test: 1) identify which existing workflow you're fundamentally transforming (not just improving), 2) pinpoint customers' deepest frustrations that keep them awake at night, 3) determine if your solution unlocks previously impossible capabilities, 4) leverage unique data advantages that create switching costs and 5) proactively address the trust problem through transparency and ethical practices. Perhaps most crucial yet immeasurable: Founders with unrelenting conviction who've personally lived the problem they're solving will outperform those merely chasing the next tech wave. Every (6 minutes)
Stripe
AI and stablecoins are reshaping finance like twin hurricanes, and Stripe is harnessing both forces simultaneously with game-changing innovations that could redefine how global business operates. 1) Stripe unveiled the world's first AI foundation model for payments, trained on tens of billions of transactions, which instantly improved card-testing-attack detection by 64% — delivering in one day what previously took two years to achieve. 2) Their new stablecoin-powered financial accounts, now available in 101 countries, allow businesses to hold balances in stablecoins, receive funds through both crypto and traditional banking systems, and send stablecoins globally, particularly benefiting entrepreneurs in countries with volatile currencies. 3) They've partnered with Visa to create cards that let users spend stablecoins at 150 million merchants worldwide, effectively bridging the crypto-fiat divide. 4) New multi-currency features eliminate unnecessary FX fees by letting companies hold and manage separate currency balances, issue cards and pay suppliers in local currencies without conversions. 5) Over 60 additional launches include support for 25 new payment methods, AI-powered dispute management and tax service expansion to 102 countries. Stripe (6 minutes)
Founder FAQ: How Do I Compensate My Board Members?
Founders often struggle with compensating outside board members, but the guiding principle is surprisingly straightforward: align incentives through ownership, not paychecks. While founders and investor board members already have skin in the game through their existing equity and investments, independent members need proper motivation to make wise decisions for the company's future. Cash compensation is a major red flag that signals misunderstanding of startup dynamics — someone demanding immediate payment likely lacks the long-term perspective essential for guiding early-stage companies. The optimal approach is granting 0.25-1% equity with a two-to-four-year vesting schedule (without a cliff), ensuring board members benefit only from creating lasting value alongside other stakeholders. Cover reasonable board-related expenses like travel to meetings, which acknowledges their contribution without draining precious cash. Consider offering (but never requiring) investment opportunities in future rounds, which deepens alignment and sends positive signals to other potential investors about company prospects. Westaway (5 minutes)
Startup Funding Guides
I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.
Convertible Note: Guide / Video
Extending Your Runway with General Counsel
In this economy, every startup is looking to lower burn rate and extend runway. We helped a Series A, generative AI company drastically reduce their legal spend by switching to our General Counsel service. When we first met the owners, they were working with a big law firm and felt they were overpaying for basic legal work. Nearly every month, they got a hefty bill just to cover equity grants, contract reviews and lawyer calls/emails. When they switched to General Counsel at Westaway, they:
Got more personal service and quicker response times.
Significantly reduced their legal spend.
With faster deal execution and lower spend, they extended runway and improved cash flow. If you're looking to optimize legal costs and extend runway, click here to schedule a call. Let's discuss whether on-demand General Counsel is right for your startup.
Post of the Week
