I was lost.

At 28, I was unemployed living in Boston with two years of professional (mind-numbing) work experience that I had no plans on leveraging. #groundzero

Having quit my back-office finance job with no safety net save the annual bonus check I stuck around for in early July, I was getting philosophical about life and figuring out my next move. My girlfriend (spoiler: now fiancé) Maggie was also at a crossroads in her career and our working plan was to move away and explore another part of the country (San Fran, Austin, Denver… anywhere but Boston). As she had a more tangible skill set (four years at a top consulting firm), we were definitely more focused on her job hunt – I would tag along and find something wherever we ended up.

As for me, this is about all I knew:

  • I seem to get most excited when I’m building things. This I had learned from making a simple iOS card game app over the previous year.
  • I need autonomy over my work and no limitations on the impact of my work. After feeling like a cog in the wheel at my previous job, this was super important for me.

With this in mind, I dove headfirst into the startup world as these small (earlier stage the better) innovative companies seemed to offer everything I was looking for. Typical days that summer were spent at the Boston Public Library researching startup opportunities in our target cities and working on coding challenges to strengthen my programming skills. There was a memorable moment as I left the library one day – unshaven in sunglasses, shorts, t-shirt and flip-flops (I’d already adopted the startup uniform) – and I crossed paths with a VP from my last company. He was mid-conversation with someone, both in suit and tie, and though we’d only worked together very indirectly, he recognized me and had the most confused look on his face.

One of the first things I did in researching startups was to create an account on AngelList. If you’re not familiar with AngelList, it’s essentially LinkedIn for startups with elements definitely drawn from dating apps – companies and individuals can show interest in each other and get notified when there’s a match. My profile listed Shnarps (the iOS card game app) as a project, but otherwise gave no indication of relevant experience for startups who came across it. As weeks passed and July turned into August, I had “matched” with a handful of companies – all of which went radio silent after I passed along my resume at their request.

So when I matched with a Boston-based company in the health and wellness space, I had no expectations for it to go any differently. This time though the response to my resume was “Can you meet on Wednesday at 1130am in South Boston?” I figured it would be good to grab coffee and pick this guy’s brain about the startup world, but they were in Boston – not part of the plan.

At 130pm on Wednesday I walked out of Coppersmith (a restaurant / coffee shop) and called Maggie buzzing with excitement. I’d spent the last two hours getting an immersive education in the current and future landscape of the fitness industry. Brett and I immediately connected on so many levels. Though he was a few years older (sorry BMo), we’d gone to competing high schools, played professional sports in the minor leagues (baseball for him, hockey for me), and generally had a similar mindset and approach when it came to breaking things down.

A couple weeks later I was progressing through the interview process, having completed a coding project and met with Brett’s co-founder Alex. As anyone who’s been involved with a company where you can count the employees on one hand knows, job descriptions are very fluid – culture fit and resourcefulness are infinitely more important than a candidate’s experience or current skill set. So while the AngelList job screened for “Lead iOS Developer”, this hire would also be the first employee and tasked with more than just converting specs into code. Fundamentally, the job was to execute on a vision with loose parameters and limitless freedom/responsibility. This opportunity not only checked all of the boxes for me, but it fired me up in ways that I hadn’t felt in years.

Through countless conversations with Maggie, we decided this opportunity was too perfect for me to pass up and we would postpone our plans to move elsewhere for the time being. It was a decision that we both struggled with for weeks. This was something we hadn’t accounted for; grabbing that initial coffee with Brett was supposed to be nothing more than a chat with someone in the startup space. Maggie’s selflessness in putting aside our plans to allow me to pursue this dream is something for which I will always be grateful.

Having no idea what I was getting myself into, I signed on to join Ladder in October 2016.

Excited, nervous, ready to take on the world.

15 months later… Here I am. Head of Product for a growing startup that now has >10 employees, anxious to see what the next 15 months will bring!

Leland Fidler

Leland Fidler

Head of Product at Ladder - Former Professional Hockey Player - Someday I want to live in a Tiny House, in the middle of nowhere.

Tiny houses are weird


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