I’m starting a new series to showcase the biggest setbacks experienced by the most successful
people I know. Hopefully you’ll see that none of us are immune to life’s whammies and maybe
we can use their lessons learned to save ourselves some time and heartache.
One of my upcoming interviews (that I can’t wait to share with you) suggested that I start the
series with one of my own stories. So here goes.
Failure Proof
Stories of setbacks and lessons learned
By the time I was 29, I had experienced a fair amount of professional success as an entrepreneur.
I had a thriving legal staffing company, was involved in several community groups, and really
felt I knew what I was doing. So I started dreaming even bigger.
I came up with an idea for a software product that would help refer attorneys to one another.
I raised nearly $500,000 in angel funding, hired a team, built the software, and convinced a
regional bar association to promote it as an internal program. I called it Legal Sonar, and — like
all startups in the 2010s — developed a cool logo and slapped it on a lot of t-shirts.
Legal Sonar sold a ton of memberships to lawyers. Signups were going so well that a venture
fund called to ask what I’d do with an extra $1.5 million in funding.
But there was a problem.
Lawyers were signing up to be featured on the platform, but they weren’t using it to actually find
other lawyers to refer folks to. We tried everything we could imagine to change behavior, but
nothing worked.
Legal Sonar was a zombie. And I had called in every favor I could, put my personal reputation
on the line to bring it to life.
We had found a big problem in the market, but our solution didn’t actually solve the problem.
And I had used most of the startup funding to build version 1 of the software. I didn’t have
enough resources left to iterate or try again.
I was so embarrassed. The failure felt so public. This was the biggest thing I had ever attempted.
There were articles about us. There were employees, investors, and partners that were
disappointed.
I spent the next three months helping my employees find new places to land. And
I promised myself that I would never again commit resources to an idea without running a
smaller test to make sure it would work. And I vowed to help others avoid the same pain and loss
by putting my lessons I learned into my first book.
Lessons Learned:
- Never commit large resources to an idea without running an experiment to understand if
your core thesis will work. - More resources aren’t necessarily better. If you’re headed in the wrong direction, they
will only help your demise be more spectacular. I think I would have benefited from more
constraints up front. - There is a direct connection between your failures and successes. This is the worst thing
that’s ever happened to me professionally and it led to the best thing: writing a NY Times
Bestselling book and starting a new career as a speaker. - Nothing is ever 100% a failure. There are always assets left over that can help you in the
rest of your career. My lessons learned turned into a book and the relationships I made
along the way are still friends and advisors today.
