Founder Fridays No. 166
Do Hard Things First -- Unlearn to Lead Forward -- Breaking Rules Builds Loyalty
Happy Friday!
Do Hard Things First
Most founders waste years selling products nobody wants because they’re talented enough to generate weak product-market fit from bad ideas. The counterintuitive move is spending your early days doing what you’re worst at—Akhund spent four months in 90 expert conversations learning fintech compliance before writing a single line of code, then took 18 months to build Mercury’s MVP when conventional wisdom said ship in three. This “doable but hard” approach paid off: someone deposited $1M four days after launch without ever contacting the team, users stayed patient through broken features, and growth sustained through a pandemic that initially killed 60% of revenue. Real product-market fit means waking up to new users you can’t explain, not grinding to convince people your mediocre idea has potential. First Review (12 minutes)
Unlearn to Lead Forward
We’re dangerously bad at being human right now, and platitudes about humanity ensuring our relevance against AI won’t save us when constant self-protection is draining the humanity right out of us. Brene Brown’s work with 150,000 leaders across 45 countries reveals that the toughest leadership skill isn’t strategic thinking or execution—it’s having the discipline and humility to unlearn what got you here and relearn what gets you there. The new essentials are deep connection, deep thinking, and deep collaboration, paired with paradoxical thinking, anticipatory awareness, and productive urgency over reactivity. Performance and wholeheartedness aren’t mutually exclusive; treating them as such is the falsehood that’s killing both individual growth and organizational transformation in our uncertainty-soaked world. Check out her new book. I just finished it and loved it. Amazon (8 minutes)
Breaking Rules Builds Loyalty
Trader Joe’s generates over $2,000 per square foot—double Whole Foods, quadruple the industry average—by doing the opposite of every modern retail playbook: 4,000 SKUs instead of 50,000, zero advertising, no e-commerce, and 80% private label when competitors rent shelf space to national brands. Joe Coulombe’s genius was spotting that post-WWII college expansion and plummeting international flight costs created a new customer: the overeducated and underpaid, hungry for discovery but unable to afford luxury. He paid employees 40-150% above industry rates, turned wine into a trust-building education tool, and sold to Aldi in 1979 with one condition—total autonomy to stay weird. The result is a company profitable every single year since 1976, with employee turnover one-tenth the industry average, proving that scarcity fuels discovery and “no broken promises in the value chain” beats scale every time. Acquired Briefing (14 minutes)
Founder FAQ: What is CIIAA and why is it important for startups?
Most startups lose expensive legal battles because they didn’t get a CIIAA signed before employees started creating code, not because the agreement was poorly drafted. This confidentiality and invention assignment agreement ensures the company—not individual employees—owns everything created during work, protects trade secrets from walking out the door to competitors, and satisfies investor due diligence requirements that can make or break funding rounds. Smart founders carve out “prior inventions” and “side projects” to attract top talent who won’t sign away weekend work, but everything else—software, business strategies, customer data, algorithms developed on company time—must legally belong to the company. Without this single document signed at hire, you’re gambling that departing employees won’t claim ownership of core IP, and no amount of retroactive paperwork will save you when acquirers or VCs discover the gap during diligence. Westaway (6 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
Is the Billable Hour Right for Startups?
Most law firms bill startups by the hour because that’s the status quo. But while it may work for big companies, the billable hour is likely the wrong model for startups. Why?
It incentivizes inefficiency. Firms are motivated to pad hours rather than work efficiently. This adds unnecessary costs.
It rewards busywork over results. Startups care about outcomes, not hours logged.
Costs are unpredictable. With fluctuating monthly hours, legal spend is hard to budget.
It stifles innovation. Hourly billing gives no incentive to find better solutions. Startups need forward-thinking counsel focused on results. That’s why we’ve ditched the billable hour for transparent flat fees.
If you’re ready to explore a law firm with a better billing model, let’s talk.