Startups For the Rest of Us Episode 555 | Businesses You Can Bootstrap, W2 vs. Contract, Enterprise Pricing, and More Listener Questions with Ruben Gamez
Jun 22, 2021
Ruben Gamez, an expert in bootstrapping and hiring strategies, joins the discussion to share valuable insights. He explores the pros and cons of hiring W2 employees versus contractors, shedding light on their long-term impacts. Gamez also evaluates what makes a business idea suitable for bootstrapping and offers strategies for competitive enterprise pricing. From successful bootstrapped businesses to strategic hiring and pricing models, the conversation is packed with actionable tips for aspiring entrepreneurs.
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Different Successful Bootstrapping Models
- Bootstrapped businesses follow different successful templates, from high-efficiency profitable niches to aggressive growth-first plays.
- Examples: Moraware (niche, high revenue/employee), CartHook (aggressive growth and larger teams), Balsamiq (long-term sustainable product).
Drip Shifted From Lifestyle To Scale
- Rob shares his pivot from lifestyle expectations to scaling with Drip as product-market fit pushed growth and hiring.
- He started Drip expecting a small team but grew to ~10 people and an eventual acquisition because the market opportunity justified expanding.
Hire Full-Time For Core Roles Use Contractors For Specialized Work
- Hire W2/full-time for core strategic roles and product development; use contractors or agencies for performance-driven or specialized work.
- Ruben and Rob recommend full-time for core devs, agencies for content/paid acquisition where multi-skill teams outperform one hire.