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Top Lessons Learned During My Entrepreneurial Journey

The conventional hiring wisdom prioritizes hard skills.

However, at a company’s earliest stages, the sheer quantity and diversity of activities that are required to get things off the ground very rarely fit squarely in one person’s suite of competencies. Daily activity also evolves rapidly, so hiring someone who meets a specific set of needs at one particular point isn’t likely to work out long term.

Entrepreneurial Journey

There are several requirements that do persist as start-ups grow: the need for curiosity, creativity, and strength of mind required to will something into existence. Cofounders and early team members need to make things happen, and I’ve learned that it’s soft skills, not hard skills, that do this—work ethic, curiosity, creativity, etc.

In my experience, the number of years under your belt isn’t important and can even be a deterrent. The naivety of young, restless people is invaluable.

It’s far easier to question why things are done the way they are if you’re new to something and aren’t weighed down by previous experience.

Choose Your Cofounder Wisely

Of course, this is obvious, and as a second-time founder, it’s certainly something I was aware of before founding Groundfloor. The 18 months during which we’ve been operating have only reinforced how important this relationship is.

Cofounders need to combine complementary skill sets, personal and emotional connections, and a long-term alignment on what they want to be doing for the next 10 years of their lives. Layered into this is the requirement that they be someone you enjoy spending time with daily. This is an incredibly hard mix.

There are so many examples from my cofounder relationship—one from just this week. At 10 p.m. on a Tuesday, after a very long day, I called my cofounder and asked, “Are we actually building something people want?” We ended up talking for an hour and determined that yes, we were building something people want, and I was having a long day.

But I needed the conversation, the reminder, and the other perspective. Being able to spend 10 hours in the weeds together and then suddenly zoom up to 30,000 feet and question everything, then bounce back into the nuances of e-mail copy and customer relationship management (CRM) optimization, is what makes the cofounder relationship uniquely valuable.

Understand the Sunk-Cost Fallacy

Most are familiar with this: the concept that people are reluctant to cancel or change a path if time, effort, and money have already been invested in it, even if changing is objectively the right thing to do. This is easy to understand but very, very hard to do!

One example for us has been the process of evaluating a property as a potential Groundfloor location. This process can be expensive and labor-intensive and can include completing designs, paying thousands of dollars to professional services, and doing extensive research.

While scouting out our second location, we went all in on one location, committing dollars and our team’s time, and got as far as final lease negotiations. But, there were red flags. We made the decision to pull out, rendering the previous month’s work obsolete, and we went back to the drawing board.

The lesson here to me is that what feels like an immediate waste of time and money (changing course) can—if the decision is correct—ultimately be significantly better than spending the time and money going down the wrong path.

Most People Aren’t Doing as Well as They Appear

People and, by extension, companies decide what they put out in the world. They’re selective, and as a result, most public information about businesses and founders is a projection of the version of the businesses or founders they want others to know.

The net impact of this is that most publicly available information on any given subject skews positive. This means that comparing yourself with others isn’t comparing like for like. You’re comparing the hard facts about yourself with the best version of something, or someone, else.

An example here is a competitor of ours that, based on its public image, we had assumed was significantly further ahead of us in the metrics we care about—member count, engagement, revenue. As it turns out, thanks to more information becoming public, not only was it not nearly as far ahead as we thought, but by most metrics, considering our relative youth, we were also doing better.

Of course, the best thing here would be not to compare yourself against others, but assuming that’s impossible, the lesson I believe is: Don’t believe the hype!

Celebrate the Wins Along the Way

Most founders are hard-wired to be neurotic and expect more. As a result, the product is never good enough and progress is never fast enough. We’re naturally tempted to wait “until things are done or are better or bigger” before allowing for celebration and public notice.

A valuable lesson I’ve learned is that this is the opposite of what you should be doing. By definition, when growing a new company, things are never done; goal posts simply shift, and the goals get larger.

Giving yourself and your team the ability to recognize the progress along the way is important not only for everyone’s fulfilment and mental health but also for others’ perception of the company—if these milestones are shared publicly.

An example for us was our revenue targets. We opened our first location in March and hit a $20,000 monthly recurring revenue (MRR) the very next month and a $30,000 MRR the following month. Over the summer, we discussed not sharing revenue updates publicly until we hit a $50,000 MRR before remembering that just a few months ago, even 10% of this felt unattainable.

We shared progress, and it led to significantly new investment into our company and a renewed realization of just how much we had accomplished so far without diminishing the amount that was left to do.

Jamie Snedden is a serial entrepreneur, an architect, and a Fulbright scholar. He started his first venture-backed company at 19 out of college and went on to lead operations and scale teams at high-growth innovative start-ups like Hostmaker, Zamna, and YC peer-to-peer rental company Fat Llama (acquired this year). He’s passionate about design, hospitality, and community.  

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