5 Things I Learned Building Lovely Direct

Over the past year I’ve worked at Lovely on an innovative new product called Lovely Direct. At a high level it was a technology product for leasing rental properties for property owners and managers. We took care of the legwork (photos, marketing, showing, screening, etc.) and let our customers make the important decisions on price and tenants. Despite impressive growth and customers loving us the Lovely SF office was all laid off January 7th and Lovely Direct is shutting down. Despite the sadness I feel for leaving such a great team, I learned a ton in this past year and I’ve tried to distill some of those learnings below in the hopes that others might benefit.

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RIP the Lovely Direct splash page

The first week of 2016 was one of the most eventful of my whole life. After a great two weeks in Maine with Kate and her family, I was ready to hit the ground running and make shit happen in 2016. But as the commercials say, life comes at you fast. Monday I got a car window smashed (nothing taken), Tuesday was my 27th birthday (an awesome day), and Thursday I found out I was out of a job. It was an amazing run in just under a year and despite having no control over the loss of our product and team, I know these learnings will leave me in a much better place — whatever I end up doing next. Among other learnings like, don’t forget to label your almond butter (shoutout Affan!) and never miss an opportunity for karaoke, here’s what I’ll take with me most from building Lovely Direct:

The pains of finding product-market fit

Our product was a new idea. Taking a traditionally entirely manual process and making it smoother with technology is exactly the type of challenge I like. I was brought on specifically to work on Lovely Direct and at first we talked about it as “the leasing project” before it had a name. We started with one operations person, Leah (hire her!), and no full-time engineers. People joked it was JLAAS, Josh and Leah as a service.

The first challenge we had was determining if this was a viable product in the first place and if the market would support us. I hit the streets and crashed open houses for two weeks straight, pitching landlords and property managers on our automated leasing solution. And…people hated it. I heard things like “this will never work” and “the leasing process will always need a human touch.” Some of this feedback hurt but mostly it was extremely useful.

We changed our rhetoric and messaging around the product and started to see people respond positively. Our first customers gave us units to work on.

These first few units were exploratory for us. What did we need to do to meet expectations and lease a unit? We had no real tech built into the product at this point. We sent emails with updates and everything was bare bones. Ultimately we found that people were pumped to have us do the work for them, even if there were bumps along the way.

One of the best things we did as we continued to build out our team was to interview everyone we worked with at the conclusion of their process with us. We learned where the real pain-points were in the process and were able to tweak our offering. Some people would rant at us about how terribly we screwed up this or that and then at the end of the interview when we asked if they would use us again they’d say “absolutely, of course.”

By the end of Lovely Direct we didn’t yet have a full-featured product but were were close. And it was all driven by this at times harsh feedback loop. When we were able to get feedback from the market, funnel those learnings internally to develop the product and inform the messaging, and then repeat the process, we scratched the surface of product-market fit.

Failure is everything

Related to the first point. Lovely Direct was the first time in my career where I realized how crucial failure is to success. It sounds backwards, but without our failures, there’s no way we could have scaled to nearly 100 units in the course of 9 months.

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Risking only personal pride and ego talking to landlords at their open houses was the best way to get rejected and learn about our assumptions at a high level. Whenever someone said no to our product, assuming it wasn’t a loud and offended “NO!” (which I got a few times), I’d ask what specifically turned them off about the product and why it didn’t work for them. Lots of those “not for me” responses led to our “sure, I’ll give this a try” answers.

As we started to nail the product and sold it more successfully, we brought on so many units that we broke our own internal operations practices. We were able to grind through those tough units and re-engineer our process for success. Breaking things and failing forced us to be more efficient.

It may not be comfortable, but pushing to the point of failure made us more efficient and helped us sell better.

Culture yields results

The Lovely office is the best place I’ve ever worked. People here were smart, driven, and really freaking fun. I talked with Doug Wormhoudt, our co-founder, at our holiday party about what he hires for and it stuck with me. He looked for people who were passionate, intelligent, curious, and humble. Everyone here embodied those traits and then some.

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Our Lovely Direct Holiday Card

The work we did was sometimes a grind but doing it with people here was always a joy. I never dreaded going into work and I don’t think anyone did. When you hire good people, foster a culture where people are pumped to show up, and let them loose, great things can happen. That’s something I’ll always remember and look for in any place I work. Without a great culture, products and businesses will always stutter.

Specifically for Lovely Direct, people would raise their hands to contribute outside of their core functions at work because they knew there was an opportunity to help the team. From taking on showings to lending a hand on operations, people cared about the team and end result more than themselves. I’ll always value and look for that in any place I work.

Bosses are important

At Lovely, I had a friend as my boss, Erik Preston (hire him too!). Erik was someone I got to know when I first looked to move out to SF. We kept in touch and he eventually convinced me to work on Lovely Direct. He told me in the hiring process that his style was to bring on smart people and get out of their way. I knew I could learn from him and thought of him as someone I could model my career after in some ways.

True to his word, he let me run free at Lovely. He removed obstacles, proactively put me in positions to grow and learn, and genuinely found me a role I could succeed in.

Up until I worked on Lovely Direct, I always thought good people can shine no matter their situation. I still believe that but I also firmly believe that a good boss can accelerate growth personally and professionally where an individual can be limited on their own.

Harsh capitalism

The toughest lesson learned. Lovely Direct was an absolute success no matter how you measure it. We had a Net Promoter Score of +20, worked with some of the biggest property owners and managers in San Francisco, and successfully leased almost 100 units in a very short time frame.

In the end, none of this mattered. The Rentpath board is controlled by a private equity firm and they made a cost-cutting move to take the functions of our office to Atlanta. This just opened my eyes in a new way. My biggest complaint about Lovely was that it wasn’t a big enough risk (larger post on that later) and that seems a little silly now.

Final Thoughts

I grew a lot in my one year at Lovely. These are great people and this experience will serve me well in my life going forward personally and professionally. Can’t wait to apply these learnings to what’s next. Long Live Lovely.

If you liked this post, please hit the little green heart to recommend. Also, if your company is hiring, there are tons of great folks from Lovely looking for great new places to work. You can find them all here.

Co-Founder @teamhandstand (The SF Hunt, The Loop). Formerly BD @Lovely and @Curious. Hustler. Over-the-hill soccer player. Find me @jzipdamonsta

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