Founder Fridays No. 113
The Catch 22 for Women in Leadership -- The Double-Edged Sword of Crowd Wisdom -- How to Make Annual Planning Suck Less
Happy Friday.
The Catch 22 for Women in Leadership
Most leadership advice tells women to be more assertive - yet studies show the more assertive a woman becomes, the more negatively she's perceived. This maddening catch-22 exists because traditional leadership structures were built exclusively for men, creating an impossible balancing act for women trying to fit the mold. When women lead with natural empathy and collaboration, they're labeled "too soft"; when they show decisiveness, they're deemed "too aggressive." The path forward isn't about finding the perfect middle ground between these extremes. Instead, the most effective women leaders are rewriting the playbook entirely by developing their own authentic leadership style, building support systems that value diverse approaches, and actively reshaping organizational cultures to break free from outdated expectations. The goal isn't to crack some mythical leadership code - it's to create new ways of leading that work for who you actually are. Psychology Today (6 minutes)
The Double-Edged Sword of Crowd Wisdom
While the "wisdom of crowds" can be remarkably accurate for objective questions, as demonstrated by jelly bean counting experiments and game show audience polls, it falls short in creative and innovative endeavors. The crowd's power lies in averaging out random errors, allowing informed minorities to guide outcomes. However, for product development and innovation, this same mechanism can lead to bland, uninspiring results that offend no one but excite no one either. Startups, in particular, should be wary of over-relying on crowd opinions, as they need distinctive offerings to carve out their niche. The key is recognizing when to leverage collective wisdom and when to trust individual vision, especially in creative and innovative pursuits. A Smart Bear (4 minutes)
How to Make Annual Planning Suck Less
Most of us treat annual planning like we're following a recipe, but that's exactly why it fails. Instead of copying frameworks from your last company, the key is designing a process uniquely suited to your business model, stage, and team composition. High-growth teams like Notion and Linear have found that constraining the timeline (ideally to 5 weeks) and starting with conservative headcount numbers prevents the endless cycles of dreaming big only to slash later. The most counterintuitive insight? Invest more time in org design than meticulous planning - the right structure gives talented teams the ability to continuously adapt toward goals rather than executing a rigid roadmap. The real challenge isn't setting ambitious targets, it's getting explicit agreement upfront on what success looks like - is hitting 70% of a stretch goal considered a win, or do you need 90%+ achievement? First Round Review (28 minutes)
Founder FAQ: What’s the Deal With Dilution?
Dilution isn't always bad. Your smaller slice of the pie might actually be worth more money – this counterintuitive truth lies at the heart of startup equity dilution. Every time you raise money, issue stock options, or convert SAFEs, your ownership percentage inevitably decreases as new shares are authorized. However, if your company's valuation increases significantly with each round, even an 10% stake could be worth far more than your original 20%. The key to managing dilution anxiety is maintaining radical transparency with all shareholders, creating a clear equity management plan, and helping everyone understand that dilution is often a necessary catalyst for explosive growth. Westaway (10 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
An Innovative Law Firm?
Being listed among Fast Company's “Most Innovative Companies” is an honor for our law firm, yet we believe innovation matters if it actually produces better outcomes for startups. Here’s how we’ve innovated to better serve startups:
Clear Pricing. Traditional billable hours can lead to misaligned objectives and unexpected fees. We've replaced this with straightforward, flat-rate pricing.
General Counsel. Most entrepreneurs want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a fixed, monthly fee so you can control your costs and focus on scaling your business.
Automation and Artificial Intelligence (AI). We've streamlined our operations through automation and AI (where appropriate), ensuring efficient, high-caliber results.
If you’re an innovative startup looking for an innovative law firm, let’s talk.