Skip to content

Here’s How My Wife Helped Me Become A Better VC

Steve Schlafman
Steve Schlafman
4 min read
Here’s How My Wife Helped Me Become A Better VC

I am a VC. My wife is a founder. When I walk into our apartment at the end of each day, my role morphs from investor to husband but I also become a motivational coach, sounding board and sometimes even a punching bag. There’s virtually no barrier separating my life from entrepreneurship. It’s a constant. I have a completely unfiltered view into the life of an entrepreneur. I see the wins, the losses and everything in between. This situation has helped me gain a deeper appreciation for entrepreneurs and the daily battles they endure and sacrifices they make.

Nearly four years ago, Eliza started The Sill after struggling to decorate our home with plants. The online options felt antiquated, uninspiring and purely transactional. The offline options weren’t any better. Plus they required serious plant knowledge and a fair amount of manual labor. As someone who always enjoyed plants and spent her career in branding, Eliza noticed that plants were effectively a commodity and that no modern brand spoke to millennials who wanted more greenery in their lives. Despite plants being a multi-billion dollar category, virtually none of the options took a design oriented and customer centric approach. Sensing a gap in the market, she decided to quit her job at Living Proof, start The Sill, and raise some cash on Kickstarter.

Fast forward four years, The Sill now delivers plants to apartments all over Manhattan and Brooklyn, operates a retail shop in the Lower East Side, services large corporate accounts like WeWork and Google, and ships nationwide. While the company’s first office was a tiny, rent-free space in Chinatown, it’s now headquartered in a 10,000 square foot industrial facility in Maplewood, New Jersey. Magazines, blogs and other media outlets have taken notice. The Sill has been featured in just about every major publication including Dwell, Better Home & Gardens, Forbes, Vogue and Refinery29. Most importantly, Eliza has built and groomed a dedicated and passionate team who truly believes in building a category-defining company. They’re like a family.

All of this has been accomplished with blood, sweat, tears and lots of dirt under her fingernails. Literally. The Sill remains bootstrapped and 100% employee owned. In this day and age, when the default seems to be shacking up with cofounders and raising large seed rounds, Eliza decided to travel the path less taken. Single founder. No investors. She, her partner and team, have built The Sill brick by brick. Every dollar The Sill has made has been reinvested in the business so it can continue to grow and thrive.

As you can probably tell I’m super proud of Eliza and The Sill. And for good reason. I have a front row seat into the life of a female founder. Not the watered down stories we all read in blogs but the real stuff. I see the stratospheric highs and deep lows. I’ve see how hard she works. Seven days a week. Three hundred and sixty five days a year. I see how much she cares about delivering an amazing experience to all of her customers, especially when they are unsatisfied. It’s clear that building a successful brand takes an insane amount focus, passion and dedication. The customers always need to come first. There are no shortcuts or overnight successes. In fact, Eliza acknowledges The Sill will be at least a decade-long endeavor.

I witness it all. Running payroll late at night. Taking calls and sending emails at all hours - even while on our vacations. Balancing the books at month end. Being treated differently by suppliers and partners because she’s a woman. Waking up at the crack of dawn to receive a truckload of plants. Creating and sending proposals to clients. Working all weekend to help at the store or a photoshoot at the office. Having an employee quit a few days before a big project. Feeling like the task list is never ending. Dealing with employee matters such as hiring and firing. Losing key clients. Worrying about running out of cash. Crying at the end of the day because some times she feels alone and that it’s just really fucking difficult. There’s very little romance when it comes to being an entrepreneur. From my vantage point, it’s a gut wrenching roller coaster ride.

Many people assume that I advise The Sill given my day job and my relationships. Honestly, I stay out of Eliza’s way. I don’t review financial models. I don’t provide criticism when I disagree with a decision. I don’t dig into business processes. I even restrain myself from pointing out bugs on the website. I realized very early on that The Sill is Eliza’s company, not mine. My job as her husband and best friend is to be present, listen and provide emotional support. I only offer advice and feedback when asked for it. I don’t give her a hard time for working too much. Sure, there are times when I disagree. But I bite my tongue, because putting my ego aside and being there for her is more important for our relationship and the company.

Over the last four years, my advice to Eliza has stayed the same. I tell her to keep on doing what she’s doing. To show up every morning and never give up. To have faith that everything is going to work out. To build a sustainable business so she can control her own destiny. To intensely focus on delivering a great product, experience and brand that her customers love. To believe in herself and her team. To live in the future rather than the past. To move swift when something isn’t working. As I am writing this, I realize most (if not all) founders could benefit from these words of encouragement from those who are invested emotionally and financially.

What has all of this this taught me and how has it helped me become a better investor? This experience has given me an insane amount of empathy for founders and has humbled me in more ways than I can describe here. My biggest learning in all of this is the impact of listening and supporting over fixing and controlling. That’s what entrepreneurs need more than anything. While I’m fortunate to work with dozens of incredibly talented and creative founders at RRE, Eliza is by far the most important entrepreneur that I work with and learn from. Being married to a founder can be frustrating and challenging at times, but it’s also incredibly fulfilling and exciting. This experience has made me a better husband and investor many times over.

Venture CapitalPersonal

Steve Schlafman Twitter

Exec coach. Writer. Student of Change.