The Interplay of Love and Business: Insights from a Professional Matchmaker

When in need of entrepreneurial guidance, I don’t seek wisdom from my mentors or investors. Rather, I turn to my mother, Rachel Greenwald, a professional matchmaker who has successfully orchestrated 850 marriages over the past two decades. Envision a delightful blend of "Fiddler on the Roof" and Harvard Business School. Given such an inspirational figure for a mother, it's hardly surprising that my initial business venture revolved around a ‘Tinder for co-founders.’ 

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The parallels between dating and starting a business are more significant than one might imagine. In both arenas, the crux is to foster authentic connections. Be it pursuing a romantic interest or sealing a deal, here are five insights from my matchmaker mother to help your business thrive and endure. 

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1. Navigating Co-founder Relationships 

The statistics surrounding co-founder relationships are rather dismal, with nearly half disintegrating within four years. The primary lesson from my mother in identifying an ideal partnership involved asking insightful questions. When conducting reference checks for potential co-founders, she suggested bypassing former colleagues and opting for their siblings instead. Her rationale was that Silicon Valley is brimming with talented engineers. Our business's success would hinge not on exceptional coding capabilities, but on the individual's intrinsic nature. And who could provide a more accurate depiction of this than siblings who've shared memorable childhood experiences? 

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2. Engaging Investors 

In my early attempts at raising seed funding for my company, I played up our team's impressive credentials, including Forbes 30u30, TechStars, Y Combinator, and Google alumni. The approach, however, fell flat. My mother then shared that fruitful conversations in dating aren't necessarily about sharing facts but about expressing authenticity. This is where the power of vulnerability comes into play. She advised being candid with investors about the challenges of raising funds in a pandemic-stricken world through Zoom. I shifted my narrative from our achievements to our setbacks, and the approach resonated with Harry Stebbings, managing partner at 20VC, who decided to invest: 

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3. Understanding Your Product 

When users log onto Zoom, they rarely contemplate the interface or the placement of buttons. Their thoughts are consumed by the anticipation of connecting with someone new and making a positive impression, hoping to form a lucrative relationship. The most adept product designers focus less on granular details and more on the user's emotional journey. While consulting on our flagship product's design, my mother emphasized the significance of making the user feel acknowledged. She urged us to concentrate on how the user would feel navigating the product, and that insight guided our design process. Our approach to new features now begins with outlining the intended user experience. The result? A user experience that resonates. As Maya Angelou observed, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” 

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4. Approaching Your Sales Prospect 

Much like the early stages of romance, you aim to make a favorable impression, armed with preparation. How can one achieve this while juggling back-to-back sales meetings? Drawing inspiration from the pre-date briefings my mother provides her clients, my company developed a tool that functions as a business meeting precursor over Zoom. Our dashboard gathers crucial information about the individual you're scheduled to meet, such as their LinkedIn profile, company, title, mutual connections, and even your email history with them. Warmly serves as a silent assistant, providing reminders of your shared interests, and facilitating effortless conversation and connection. Interestingly, some of our users have also employed our tool for their virtual first dates! 

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5. Growing Your Business 

What motivates people to go on first dates? It isn't to dazzle their date to the greatest extent, treat them to an extravagant dinner, or aim for a first kiss. Ideally, the goal is to establish a relationship that is mutually beneficial. The most valuable insight I've gleaned from “business dating” is the importance of laying a solid foundation for long-term relationships. For instance, my former supervisor at Google, whom I worked tirelessly for, became one of Warmly's initial angel investors. A college friend undertook a covert operation to acquire our domain name, Warmly.ai. I met Elizabeth Weil, managing partner at Scribble Ventures while seeking running companions in Palo Alto. She not only became our initial investor but our families even vacation together. Oftentimes, new acquaintances may not turn out as expected, yet they can lead to something even better. 

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You can never predict whether the person you're meeting will become your future co-founder, employee, or even the future partner of your best friend. The key, much like in dating, is to prioritize building a relationship. With that foundation, every other aspect will be exponentially more fruitful. Thanks Mom.

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