Closing and contact info

Two years. Almost no revenue. Tito Goldstein and his co-founder Arjun raised $3 million to build a scheduling tool for hourly workers. But when they took it to market, customers kept telling them the same thing: we need to stand out, not use cookie-cutter software. So they made a call that most founders would never risk - throw it all out and start over.

The rebuild took a year. But when they launched the new version built on composable Legos instead of fixed features, it outsold the previous two years in the first month. Then it 3x'd, and 3x'd again. That's when Tito knew they'd finally found product-market fit.

TeamBridge is now doing multiple seven figures with over 200 enterprise customers, including the San Francisco 49ers' Levi's Stadium and medical staffing agencies scaling to multimillion-dollar businesses with almost no admin staff.

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🔑 Key Lessons

• 🎯 Listen to what customers don't say about product-market fit: Buyers kept asking for features, but the real pain was "I need to stand out." Reading between the lines unlocked their product-market fit breakthrough.
• 📉 Throw out sunk cost when finding product-market fit: Two years of work became irrelevant when they realized connective tissue (automations, workflows) mattered more than scheduling.
• 🛠️ Composability wins in competitive markets: Off-the-shelf tools make you a commodity. Customizable workflows make you a differentiator in the race for product-market fit.
• 💰 Stay lean until product-market fit: TeamBridge kept a team of 5-6 with multiple years of runway, giving them freedom to pivot without investor pressure.
• 🚀 First products validate problems, not solutions: The scheduling tool failed but uncovered the real pain. Use early products to learn, not scale, on the path to product-market fit.

Chapters

• Introduction and favorite quotes
• What TeamBridge does and who it serves
• Why composability matters for workforce software
• Size of the business: revenue, customers, team
• Origin story: interviewing Uber drivers
• Going door-to-door to understand hourly worker pain
• Raising $3M seed with just a prototype
• Why it took 2 years to find product-market fit
• The pivot: from scheduling to composable Legos
• First significant sale during COVID
• Biggest objections: explaining composability
• Finding the right messaging and storytelling
• Downsides of casting too wide a net
• Moving upmarket to enterprise customers
• How COVID forced TeamBridge to mature go-to-market
• Cold email lessons: honesty and relationship building
• Discovery-first selling: hold the pitch until you know the pain
• Learning the nuances of each vertical
• Lightning round: grit, curiosity, and fitness

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Resources

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