Founder Fridays No. 195
Fight or Lose Them -- Your Absence Is The Metric -- Research Wins the Room
Happy Friday.
I had a blast hanging out with the Founder Fridays communities at a happy hour in San Francisco this week. Thanks to everyone who came out.
Fight or Lose Them
Your best startup hires won’t quit over a bad salary — they’ll quit because you never pushed back hard enough on anything. Entrepreneurial people are builders, not extractors — they measure you by your willingness to fight for what’s right, and they read your silence or agreeableness as a character flaw, not a virtue. This week: pick one thing your team is doing wrong, say it plainly and publicly, then watch who argues back — the ones who push back hardest are likely your most valuable people, not your problem hires. You’ll retain the people who can carry you through a platform shift — the exact ones every well-funded competitor is actively trying to poach right now. Stay Sassy (7 minutes)
Your Absence Is the Metric
How long you can disappear without things breaking is a more honest measure of your leadership than how many people depend on you daily. Being the person everyone comes to isn’t leverage — it’s a ceiling; real scale happens when your team can solve novel problems by internalizing your principles, not by pinging you. Book a week fully offline in the next 60 days, tell no one to escalate to you, and debrief afterwards on every decision that stalled or went sideways — those gaps are your leadership debt, and fixing them is the actual work. You get a company that can move fast while you’re heads-down on the things only you can do — raising a round, closing a key hire, or figuring out your AI strategy — instead of one that freezes every time you step away. Boz.com (4 minutes)
Research Wins the Room
The thing that separates funded founders from the rest isn’t the deck or the numbers — it’s walking in knowing what this specific partner said on a podcast eight months ago about your exact category, and that’s now a two-minute prep task, not a two-hour one. VCs invest in 4 out of every 1,000 introductions they see, and the filter isn’t your market — it’s fit with how one specific human thinks; a six-prompt Claude pipeline that sequences fund thesis → partner background → objection map → portfolio signals → framing brief → one-page doc gives you that picture before you sit down. Before your next investor meeting, run just the first two prompts from this piece — fund profile and partner background — paste the outputs into a doc, and identify one thing the partner has said on record about your category that you can reference or directly address in the room. Founders who show investors they’ve done this level of prep trigger a different conversation — not evaluation mode, but engagement mode — and that shift is what moves a polite 45-minute meeting toward a follow-up ask. The Founder Corner (8 minutes)
Founder FAQ: What Are the Prime Tasks For the Board of a Startup?
The equity grants, exec hires, and major contracts you’ve already made without a paper trail are quietly sitting in your cap table like ticking clocks — and they’ll blow up the moment a serious investor runs due diligence. Board consents aren’t bureaucracy — they’re proof that your company made its biggest decisions legally and intentionally, and sophisticated investors use them to decide whether you’re fundable or a liability. This week, ask your lawyer to audit the last 12 months for any equity grants, key hires, major contracts, or financing decisions that lack a signed board consent — then get retroactive consents drafted before your next fundraiser kicks off. Due diligence moves faster, investors trust you more, and you don’t lose a round — or a valuation — because a lawyer found a governance gap three days before term sheet signing. 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.