November’s theme at Gildre: Building Team & Operations!
Behind every thriving startup, there’s a mix of strategy, structure, and people who make it happen.
We’re unpacking lessons from hiring right to building systems.

Dive into the content and see how other founders are scaling smarter.

Join our November Event: The Founder Mindset for Networking, hosted by Carol Palombini; later today, Thursday November 20th. Together we’ll explore how a shift in mindset and communication can help you connect more intentionally with other founders and investors.

To sign up, become a member at gildre.com.

Founder Mistakes When Building an Early Team

1. Optimizing for Titles and Equity Over Contribution
(The "Badge Collector" Mistake)

This involves giving away excessive equity or inflated titles (like "Chief Marketing Officer") too early to attract talent, without clearly defining roles, responsibilities, and performance milestones tied to that compensation.

Why it Happens:

• Scarcity: Feeling like they must over-compensate with equity/titles because they can't offer a competitive salary.

• Desperation: Overvaluing a candidate's potential contribution.

  Consequence: Significant dilution of the founder's ownership too early, and creating a culture where people value their title (prestige) over their actual work and impact (contribution). This leaves little room for future, critical hires.

2. Neglecting to Hire Complementary Skills
(The "Mirror Image" Mistake)

Founders often hire people who are very similar to themselves, either in personality or skill set. For example, a technically-minded founder will hire another engineer, leaving a critical void in areas like sales, marketing, finance, or HR.

Why it Happens:

• Comfort: It's easier and more comfortable to work with people who "get" your expertise.

• Oversight: Underestimating the immediate need for non-technical or "business" roles, believing they can handle it themselves.

  Consequence: An unbalanced team that's great at one thing (e.g., product development) but fails at others (e.g., product-market fit or monetization), stalling growth.

3.Hiring for Speed Over Fit (The "Warm Body" Mistake)

This is perhaps the most common mistake. Founders, feeling the pressure to execute quickly, hire the first person who seems qualified or available, prioritizing speed over a thorough evaluation of cultural fit, long-term vision alignment, and actual skill-depth.

Why it Happens:

• Urgency: The intense pressure to hit milestones or secure funding.

• Inexperience: Lack of a formal hiring process or recruiting expertise.

• Networking Bias: Hiring a friend or former colleague without fully vetting if they are the right fit for the current startup phase.

  Consequence: A toxic or misaligned culture, low productivity, and the eventual, painful need to terminate a co-founder or early employee, which is incredibly disruptive and time-consuming.

Groupon was one of the fastest-growing companies in history, reaching a valuation of over $1 billion faster than any company before it. However, the pressure to grow quickly led to fatal errors in building its early sales and operational team. Below we outline some of the mistakes they made and what they did to address them.

The Unsustainable Model (Deals were too deep, leading to merchant burnout and high churn.)
Focus on Profitable Local Experiences
Hyperlocal Focus & "Things to Do": They doubled down on the Local category (experiences, services, restaurants) and divested from lower-margin businesses like physical goods (Groupon Goods). The focus is on offering "unbeatable value" that encourages future bookings, not just a one-time transaction.

Mistake #1: Hiring for Speed over Fit (Lack of operational structure and financial controls led to chaos.)
Focus on Platform Modernization
Tech Stack Overhaul: They are migrating away from legacy systems to a modern, efficient, and agile platform. This reduces the need for constant, expensive manual intervention and improves financial reporting (fixing the early accounting issues).

Mistake #2: Neglecting Complementary Skills (Focus on sales neglected the long-term customer experience.)
Enhancing Customer Lifetime Value (CLV)
Personalization & Retention: Instead of just acquiring a customer with a cheap deal, the goal is to drive repeat purchases. They use data and AI to personalize offers, improving the user experience (UX) and increasing the customer's frequency and engagement.

Mistake #3: Optimizing for Volume/Titles (Hiring thousands of sales reps quickly to chase any deal.)
Pivot to "Quality over Quantity" as a Merchant for Self-Service & High-Quality Vetting: They no longer rely on a massive, unmanaged sales force. They focus on providing high-quality tools for merchants to manage their own deals, and rigorously vet deals to ensure they are beneficial for both the customer and the merchant.

If you’re leading a team or just trying to figure out how to make yours work better, this talk’s for you. It’s about People-First Product Leadership, but really it’s about how great teams are built through trust, listening, and showing up as your real self. The speaker reminds us that leadership isn’t about having all the answers, it’s about creating space for others to shine. Super insightful if you care about building teams that actually enjoy working together.

The most costly mistake founders make is prioritizing speed and volume over quality and fit in their first ten hires. The stories of companies like Groupon (operational maturity) confirm that the initial team defines the company's DNA and its ability to scale sustainably.

If you’re interested in learning more about the Gildre Community you can schedule a conversation with Managing Partner, Taiga Gamell here.

Cheers,
Eliana