Founder Fridays No. 124
2024’s Biggest Tech Flops -- Who Will You Be In 2030? -- Founder Questions That Matter
Happy Friday.
2024’s Biggest Tech Flops
Most startup post-mortems read like obituaries, but the most instructive failures of 2024 reveal a deeper truth about our industry's collective blind spots. From Google's over-engineered inclusivity causing their artificial intelligence (AI) to generate historically inaccurate images to Bowery's $700 million bet on vertical farming crumbling under the weight of basic plant biology, what we're seeing isn't just failed execution — it's failed assumptions about what technology can actually solve. The story of 2024's biggest tech failures also exposes how cheap capital masked fundamental business model flaws, with companies like 23andMe and Running Tide discovering too late that having users or good intentions doesn't automatically translate to having a sustainable business. Perhaps most tellingly, the year showed how our industry's "move fast and break things" mentality can spectacularly backfire when applied to critical infrastructure, as seen in CrowdStrike's system-wide crash that grounded thousands of flights. MIT Technology Review (11 minutes)
Who Will You Be In 2030?
Most of us vastly overestimate what we can achieve in a year but dramatically underestimate our five-year potential — and this mental trap is costing us our most ambitious dreams. Instead of writing resolutions that feel like wishful thinking, the real game-changer is creating a "Self-Determination Flowchart" that explicitly connects today's micro-habits to your desired five-year outcomes. Simply visualizing fantasy outcomes isn't enough — the magic happens when you map backwards from each life domain (career, health, relationships, etc.) to identify the specific weekly actions that will compound into massive change. By linking your ambitious 2030 vision to measurable behaviors you can track today, you transform vague hopes into an executable strategy. Hackernoon (4 minutes)
Founder Questions That Matter
Real-life advice from founders like Zapier's Wade Foster, Raw Signal Group's Melissa Nightingale and Superhuman's Rahul Vohra reveals that the most transformative startup decisions often start with a deceptively simple question. When founders ask "If we close 100 more deals just like this one, will we be happy or sad?" they're forced to confront whether they're building a business they actually want to run, not just one that works. The seemingly innocent query "Are we winning because we're making good calls, or in spite of ourselves?" challenges leaders to separate lucky breaks from genuine strategic wins. And perhaps most tellingly, "What's the conversation I'm avoiding?" cuts straight to the heart of what's really holding the company back — because every founder immediately knows the answer, even if they wish they didn't. First Round Review (14 minutes)
Founder FAQ: Should My Startup Hire Someone as an Employee or a Contractor?
Most founders get worker classification dead wrong — and with state labor departments ramping up enforcement, that mistake now costs more than ever. The real difference isn't about cost or expertise but rather lies in control: Employees follow your playbook while contractors write their own, and mixing these up can trigger massive penalties and back payments. The smart move is to hire employees for core functions where you need to direct the "how" of the work, while keeping contractors for specialized projects where you only care about outcomes. Founders who try to save money by classifying core team members as contractors are playing with fire — those "savings" can turn into crippling fines and legal headaches overnight. Westaway (8 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.
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