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Design Sprint

From stuck to sold: how a design sprint transformed a startup


“I’m 24. The only mommy I know is mine!”

That was Josh Milstein’s reaction when, together with his team, they came up with an audacious pivot for his website during the design sprint process.

But let’s start at the beginning, and you’ll see how a design sprint approach can get a business from stuck to sold.

Pentalog helped Mommy Dearest with a design sprint


Helping neighbors communicate better

When Josh Milstein first approached Pentalog’s Jeff Mignon, about seven years ago, he had a simple idea: he wanted to build a website to help people living in the same building communicate better.

Jeff and his team built the website. But one year later, the site wasn’t getting any traction. None.

In spite of this, Josh was not done. His desire to build a community-building website and app was still as strong as ever.

So he talked to Jeff again.


A design sprint to the rescue

What Jeff suggested was a design sprint process to analyze the situation, and get the business moving again.

During the design sprint, which lasted about a week, it quickly became clear that the original idea was dead.

Yet, the existing website and app offered powerful functionalities, waiting to be put to good use.

What could that be?


Tourists or mommies

Who needs local content created by local advisers?

Two targets emerged: tourists and mommies. The problem with tourists is that they are… tourists, in town for a usually short period.

Mommies, on the other hand, are more consistently interested in getting local advice, and for a longer time.

This gets us back to Josh’s initial reaction: he didn’t know the first thing about mommies.

But the idea carved its way into his entrepreneurial soul.


A Yelp for NY mommies

Josh was willing to pivot his business to an app that would get local info from local moms to other local moms.

An app through which local moms could tell other moms (and dads) if a park is, for example, safe, kids friendly, or if it has a pool.

An app that would tell you what local people think about different local spots.


Mommy Nearest was born. A true Yelp for NY mommies.


From NY to other cities

The success of Mommy Nearest has been phenomenal. The mommies and parents from 15 US cities can now benefit from reliable local advice.

And last October, Josh published this on Facebook:

A few days ago, we announced that @mommy_nearest had been acquired by @kidpass, thus marking the end of an incredible chapter of my life. Building a startup has its share of both thrills and challenges, and as products evolve, teams grow, and stakes get higher, it is easy to lose perspective on the journey itself. After a few days of reflection on the last seven years, one thing continued to stick out to me, and that was all of the incredible people that I had the privilege of getting to work with day in and day out. To everyone who came along for the Mommy Nearest ride, I can only say how humbled I am to have gotten to work alongside you and how thankful I am that we got to share in the highs and lows together. I can’t wait to take the next step with the amazing team at KidPass and continue to reimagine how technology can make parenting even easier.


The power of design sprints and pivots

What the story of Mommy Nearest illustrates is the game-changing power of using the design sprint approach to find solutions or new paths for a project or business.

It also proves that a well-thought pivot can breath new life into a business that is seemingly dead or seriously stuck.

The design sprint allowed Josh to identify the true power of his idea, and the target market that would truly benefit from it.

It allowed him to repurpose a website and its app towards a promising new North Star.

What can you achieve a design sprint? Let’s find out.

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