“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.” – Steve Jobs, Stanford Commencement Speech, May 2005

One of the most common questions I’ve heard over the past few weeks from younger members of our community, especially students, is how to build a career in startups. Unlike climbing the corporate ladder, it’s not a straight forward, linear process. As I just made a major move in my career to join KISSmetrics, I’d like to share how I ended up going from Boston startup connector to SF Product Manager.  This will also help answer questions I know some of you have about how I landed this job.

Connecting the Dots – The unorthodox journey of one startuper

To really begin this story, you have to go back to my days at oneforty. When I joined oneforty, I was given the title of Customer Development Manager and asked to help make oneforty a Lean Startup. Since I had only spent a few months working part time with John Prendergast as his cust dev intern, I really had very little experience. Laura Fitton, oneforty’s founder, took a leap of faith I could learn it, but she also was wise enough to know I could not do it alone.  That’s why she set me up to have mentors from day 1.

Immediately upon starting at oneforty, Laura connected me with two Valley Lean experts she got to know while she was out west raising money for oneforty and Pivotal Labs worked to build V1.0 of the site.  These people were internet mentor legends, Dan Martell and Hiten Shah.  Once a month I seemed to find myself on the phone getting what I would happily call an “ass-kicking” from Dan helping me realize all the things I was doing wrong and most importantly, could do to improve my custdev methods.  Roughly every other month I would have a similar discussion with Hiten.

These discussions were priceless in my career development. I would take copious amounts of notes and seriously reflect upon what Hiten and Dan discussed with me each time. I would also share these notes with Laura to make sure I truly understood them and to force myself to teach someone what I learned (a great tool for deepening your understanding).

A Chance Meeting

Fast forward 12 months at oneforty and it is April 2011. I’ve learned a ton about customer development and lean startups, enough that Trevor Owens, founder of Lean Startup Machine (which was just getting off the ground at the time) invited me to be a mentor at the Lean Startup Machine event in New York City. As destiny/fate/karma would have it, Hiten Shah was also one of the mentors for the weekend.

Being a mentor traveling in from another city is very different from mentoring in your home city. When you’re in your city, you likely only stop by for a brief period of time that fits your schedule. But, when you go to another city, you find you spend the vast majority of your time there…which both Hiten and I did in New York City.

After Saturday’s activities wrapped up, all the mentors went out for drinks.  This turned into an audition and test for me.

With Hiten Shah to my right and Patrick Vlaskovits (co-author of the awesome Lean book at custdev.com) grilling me on all sorts of topics from lean startups, to lessons learned at my first real startup job to topics on psychology and body language.  At the time I was dead set on leaving oneforty to start my own company so all Hiten said was, “if you raise money for your idea, come out west and I’ll give you some intros.”  He also encouraged me to quit ASAP to start doing my own thing if that’s what I was passionate about. Coincidentally I did just that on Monday back in Boston.

Out on my own, but on the Radar

After leaving oneforty, I set out to start my company I’ve always dreamed of.  After spinning my tires for 6 months though, I found myself pretty empty handed and a bit discouraged. After a meeting with Sim Simeonov, I refocused my efforts on the lean startups movement.  After a month of interviews and discussions, I published the results, which caught Hiten’s eye when they were tweeted out.

Hiten DM’d me after my first post and we had a call to discuss my findings, which confirmed his suspicious: Lean as a concept is far ahead of actual solid execution of it in the startup world. At the end of the chat, I mentioned that I was planning a trip out to the Valley in early December and asked if we could meet while I was in town.  He agreed.

Meeting in SF and an Offer

When I met with Hiten in December during my Valley trip, we barely talked about KISSmetrics or my potentially working there. The vast majority of our one hour chat was about my strengths and weaknesses and where I was at in my startup career.

Hiten tried to sell me on the idea that coming to the Valley would solve many of my problems, but I presented a series of challenges that I felt prevented it from being the right decision for me.  He countered I could come work for him and it would resolve many of them. I noted the offer, and it did intrigue me, but it mostly sat just sat in the back of my mind.

By the end of the trip, I was much more interested, thinking it may be the next logical step in my career. On the flight back, I emailed Hiten expressing great interest in the role, especially as I discovered I could potentially be filling the shoes of the departed Cindy Alvarez (who just weeks before my visit had left KISSmetrics to join Yammer).

Getting Serious

With the holidays fast approaching, Hiten and I took things slowly, talking about the the potential first in loose terms then in much more specifics. After one phone call where Hiten lifted the proverbial kimono on everything I wanted to ask regarding KISSmetrics as a business, all that was left was an answer to the question, “When can you come meet more of my team for an interview?”

With that, I booked tickets to take a quiet trip to SF for the interview in early February.

Sealing the Deal

With an interview scheduled and a focus on landing this job, I employed my proven job acquisition system that requires me to produce, insightful, valuable content for KISSmetrics.  I happened to be reading a psychology book at the time and so I produced a massive document on different ways KISSmetrics could improve their site based on the principles I found in the book.  I also aggregated all my lean learnings in one place so the rest of the team could see the credibility in Lean that Hiten knew I had.

I wasn’t sure what to expect in the interview. All I had were the names of the people I would be talking to and a vague idea that we’d talk about the KISSmetrics product.  Most of the interview turned out to be focused on implementation: how would you do this, what’s wrong with that, what would you do in this circumstance.

Despite not really preparing for such questions, I was able to crush the interview for one simple reason: the last startup idea I had worked on was a Lean Product Management tool.  While the idea didn’t pan out, it led to me talking to 40 people who run product at companies. Through this, I picked up on many best practices and common mistakes. I was armed with more than enough fodder for the interview and believe I’m really armed to take on my first full time product role.

Conclusion – You Never Know…

Whether it’s lessons learned in a failed startup idea’s customer development interviews or an event you’re randomly invited to in another city, you never know what will lead to the next great opportunity in your career.  Startups are all about embracing serendipity. Embrace the machine and you never know where you’ll end up.

Do you have an example of unrelated events that looking back were instrumental in a step or moment in your career?