Founder Fridays No. 122

First Board Meeting After a Raise

Post-fundraising is when the real work begins, but you already knew that. You’re off to the races, hiring new faces and trying to grow sales so you have good news to share at your first board meeting. Sasha Orloff (YC W12), CEO of Puzzle, has a tip for you. The first board meeting is a pulse check on you as a founder. Your investors and advisors are looking for reasons to complain: “You’re growing too slow.” “You’re not charging enough.” “You’re going after the wrong customers.” At this stage, being imperfect is okay but being unprepared is not. And knowing the nuances of how to run a board meeting is a key part of this preparation. Here is a Startup Board Meeting template to help showcase the status of Puzzle at their first board meeting after our $30 million Series A. This is the EXACT template they still use today. Puzzle (5 minutes)

How to Sabotage a Meeting (According to the CIA)

In 1944, the CIA wrote a how-to manual for sabotaging meetings, and it was recently declassified. There’s a lot of fun stuff in here, much of it timeless. Here are some of my favorites: 1) Make “speeches” — Talk as frequently as possible and at great length. Illustrate your “points” by long anecdotes and accounts of personal experiences. 2) Slow it down — advocate caution, avoid haste. 3) Where possible, refer all matters to committees (never fewer than five) for “consideration.” 4) Bring up irrelevant issues as frequently as possible. 5) Haggle over precise wordings of communications, minutes and resolutions. 6) Refer back to matters decided upon at the last meeting, and attempt to re-open the question of the advisability of that decision. Authentic Communications (5 minutes)

Intellectual Honesty in Startups

The path to startup success requires confronting uncomfortable truths rather than clinging to optimistic delusions. Bob Moore's journey across three companies reveals how intellectual dishonesty - from dismissing competition to rationalizing poor metrics - can limit a startup's potential. His framework emphasizes choosing co-founders who challenge your thinking, measuring founder-market fit through interest and ability, validating ideas through forced-choice feedback, and recognizing when ego blocks strategic opportunities like mergers. True product-market fit transcends friendly customers writing checks - it emerges when users willingly spend their social capital promoting your solution. First Round Review (14 minutes)

Board Meeting Pre-Read

A good board meeting pre-read is a comprehensive document distributed to board members several days before the meeting. It typically includes key updates on sales, technology, manufacturing, finances and personnel. The sales section covers current performance, pipeline, major accounts and near-term projections. Technology updates focus on priorities and upcoming releases. Manufacturing information highlights key partners and progress. Financial data includes the balance sheet, profit and loss (P&L), and cash forecasts. The people section covers recent and planned hires, as well as any significant departures. This pre-read allows board members to arrive at the meeting well-informed, enabling more productive discussions on strategic topics rather than spending time on basic reporting. AVC (4 minutes)

Simple Beats Clever

You may be too clever for your own good - sometimes the smartest founders build the hardest products to understand. While founders obsess over differentiation and technical wizardry, the most successful products can often be described in just two words using the simple formula of [adjective] + [noun], like "electric car" or "smart phone." Moving up the complexity scale from "OK got it" to "WTF," products become increasingly difficult for customers to grasp, especially when founders lead with technical details, MBA frameworks, or convoluted product strategies. The solution is surprisingly straightforward but often painful for founders: show your product to target customers, ask them to describe it to others, and embrace their simpler, unvarnished truth - even if it means stripping away your clever strategic positioning. Andrew Chen (5 minutes)

Lambda: A Cautionary Tale

This article presents a compelling cautionary tale that founders must read, chronicling the rise and fall of Lambda School, a coding bootcamp founded by Austen Allred that promised to teach programming skills with no upfront costs through Income Share Agreements. Despite initial hype and significant venture capital funding, the school faced numerous controversies, including misrepresented job placement rates, subpar education quality and legal troubles. The article details how Lambda School's business model ultimately failed, with poor student outcomes and financial losses leading to layoffs, rebranding and eventual regulatory action. Finally, it explores Allred's role in the company's downfall, highlighting his tendency to misrepresent facts and his inability to address the fundamental issues plaguing the school — serving as a stark warning to aspiring entrepreneurs about the dangers of prioritizing growth and hype over delivering genuine value and maintaining ethical practices. Sandofsky (22 minutes)

How to Be A Super Communicator

I loved this interview about learning how to be a “supercommunicator” with Pulitzer-prize Winning and Best-selling Author Charles Duhigg. My experience is that as your level of responsibility grows in any organization, your success mostly depends upon your ability to connect and communicate. I’d always assumed that supercommunicators were just naturally gifted / charismatic speakers. Surprisingly, this is not the case. It’s a skill that we can all learn. In this conversation, we cover: 1) How to win someone over without challenging their identity. 2) Practical tips for difficult conversations. 3) How to ask great follow up questions. 4) Why data from experts rarely changes people’s minds. YouTube (45 minutes)

VC Partner Meeting Playbook

Most founders are flying blind into their first venture capital (VC) partner meeting. Partner meetings, a critical yet opaque part of the fundraising process, differ significantly from initial one-on-one investor pitches in length, attendees and preparation. Founders should leverage their point partner as an ally, preparing for in-depth questions and frequent interruptions while managing time effectively. Success hinges on the ability to shift between high-level vision and granular details, bringing energy and authenticity to the pitch while focusing on what truly excites investors about your company. First Round Review (22 minutes)

Endurance Trumps Intelligence

Entrepreneurship is a test of endurance, not intelligence. Starting and running a business is hard — like, really soul-crushingly hard. It feels like the universe is constantly testing your limits. It's rejection, disappointment and late nights fueled by cheap coffee and sheer stubbornness. It's wanting to throw in the towel more times than you can count. But something magical happens if you hang in there long enough. You survive those seemingly impossible moments. You develop this mental toughness that can't be taught in a classroom. And that, my friends, is where intellect finally gets to shine. When you've faced the fire, all those smarts become truly dangerous. So, what does this mean? A few things: 1) You don't have to have the perfect plan. No business model survives first contact with reality anyways. 2) Action trumps ideas. Start moving, start messing up, start learning. You can refine your intellect as you go along. 3) You're probably tougher than you think. It's shocking what you can put up with when you decide not to quit. Maybe a better perspective is: "Entrepreneurship is a test of endurance that unlocks the power of your intellect." Scott’s Newsletter (8 minutes)

Gen Z Broke the Marketing Funnel

Over the last few decades, marketers have focused their efforts around the consumer funnel. The potential customer moves through the funnel in the following stages: awareness, interest, desire, action. The funnel was built for the old world, and Gen Z doesn’t live there anymore. Instead, they live in an infinite loop of inspiration, exploration, community and loyalty. Of course the main driver is that Gen Z is spending a ton of time on YouTube and TikTok, and that’s influenced how they make purchasing decisions. As a result, retailers are behaving more like media companies. Surprisingly, despite their reputation as digital natives, Gen Z shoppers still value in-person experiences. Seventy-four percent of Gen Zs think in real life (IRL) experiences are more important than digital ones (compared to 66% of millennials). Though they conduct in-depth research online, 73%of Gen Zs prefer making a purchase in a store while shopping. This article is chocked full of insights and is essential reading for anybody running a consumer-facing brand. Vogue (17 minutes)

Founder Mode Versus Manager Mode

Conventional wisdom on scaling startups might be fatally flawed. The standard advice of hiring skilled professionals and giving them autonomy often empowers expert manipulators who can drive companies into the ground. Successful founders report feeling gaslit from both sides — advisors pushing them toward hands-off management and employees exploiting this approach. Embracing a more-involved "founder mode" may be key to maintaining the innovation and agility that drove initial success, leveraging the founder's unique insights and vision to prevent disconnected teams from steering the company off course. Paul Graham (8 minutes)

Founder FAQ: What’s the Difference Between an Employee and Contractor

Many founders falsely believe their workers are contractors just because they work remotely or part-time. The core distinction lies in control - employees work under your direction with set hours and processes, while contractors maintain autonomy over how they complete their work. Beyond this fundamental difference, employees receive benefits like health insurance and tax withholding but cost 25-35% more, while contractors offer flexibility and lower overhead but bring significant misclassification risks that can bankrupt early-stage startups. California's strict ABC test and growing regulatory scrutiny mean getting this wrong isn't just expensive - it can destroy your business with retroactive penalties, benefits payments, and legal fees. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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.

Founder Fridays