In a day when the definition of success is achieving profits above all else, there are a few refreshing examples of entrepreneurs who are enjoying success while also creating businesses that make an impact in the world. These entrepreneurs prove that impact and profits can go hand in hand.

I recently met Isa Watson, founder and CEO of Squad, and a member of the 2017 class of Inc. 30 Under 30. Her story, and Squad's success, is impressive. For starters, Watson founded Squad (then called Envested) and landed Jet.com (acquired by Walmart) as a customer in less than 18 months. Secondly, Squad is built on a mission to foster community and connection - both things that society needs in an increasingly disconnected and digital world.

As an entrepreneur, I'm drawn to understand how such rapid success was possible, and how impact was maintained as a focus. I interviewed Watson to find out what she did, why she did it and what she's learned in the process. The lessons are profound, and we can all implement them to create more success for our businesses and professional lives.

The Interview

Andrew Thomas: You're an MIT graduate and you had a great job at JP Morgan. Why did you leave that life to start Squad?

Isa Watson: At JP Morgan, I was able to get fantastic training, and because of the role I was in, I was able to gain exposure to many parts of the organization. I've always been driven to solve big problems and my experience there allowed me to do just that.

However, traveling across many different offices in the bank, I saw that the offices that had the strongest natural workplace engagement--offices where employees organized amongst themselves to go on runs or grab a drink after work--were our strongest performing divisions. And that wasn't just a coincidence. Connectivity is such a driver of productivity.

Really, it was this insight that led me to leave to start Squad. I saw a business opportunity that could be scaled to a huge degree with tech behind it--and at the same time could make a real difference in people's lives.

Thomas: You started Squad and closed Jet.com as a client in less than 18 months. How did you do that?

Watson: Before we closed Jet as a client, we made a lot of mistakes in our sales pitch and got back a lot of nos. 320 to be exact. Many of these were in part because we were focusing on the wrong type of customer. Rather than selling to early adopters--people with risk tolerance to try out a new software--we spent a lot of time focusing on what Geoffrey Moore in Crossing the Chasm calls late majority buyers. After a spell of rejection, we looked at the feedback we were getting to unpack the qualities that would make for a good client at that point in our growth. Then we took a step back and repositioned our approach to sell to them.

Jet was part of this first wave of repositioning. Although they had recently been acquired by Walmart, Jet still has a startup mindset and was right in line with our target customer at the time. From there, it was all about a combination of hustling to reach out to people who could connect us with the right partners and doing our research to make sure that our positioning was thoughtful and relatable.

Thomas: Like so many entrepreneurs, you faced plenty of rejection. How did you overcome rejection to create your success?

Watson: For me, mindfulness was really key in overcoming the almost continual stream of rejection. Rather than spiraling into negative comparisons, I focused on being grateful for how far I'd already come. I also made a point to be generous and even let go of my mistakes so I could focus on what really mattered: a mindset fixed on growth.

Another thing that was helpful was making sure I was surrounded by the right type of people in my personal life. Over the past two years, I've gone through a pretty dramatic shift in my social circle because when you get rejected every day, you become pretty sensitive to negativity. Being able to cope with that kind of rejection day after day depends a lot on who you surround yourself with.

Thomas: After a number of B2B successes, you shifted your focus to consumers. Can you share more about why and how that happened?

Watson: Even after a number of B2B successes, we decided to shift away from an exclusive focus on enterprise sales. This was really because we learned that we were wrong about a major assumption: that people wanted their work communities isolated from the other facets of their lives. The more we looked at different behaviors and the more we conducted user research, the more we saw that people want an integrated experience. People are part of many communities--at work, in their neighborhood, in their alumni groups, in their book clubs and running groups--and we saw that people wanted a place where they could bring together these parts of their lives together in one place.

Thomas: It's clear that impact is a big part of your focus. What does impact mean to you and what has it meant for your success?

Watson: For me, and in the context of Squad, impact has been all about deepening the human experience through real connections and community. If people can feel more in touch with the different aspects of and people in their lives, it's not only a driver of productivity, it also gives greater meaning to the hustle we all face.

In terms of my own success, building a product that puts community and positive human interactions first means that impact is tied with our growth. The more people that use Squad to find community, hopefully the more people find connection in their daily lives. In fact, as the experience on our platform has evolved to become even more human-minded, we've seen growth in the adoption with these developments too.

Thomas: Finally, what role did your network play in your success?

Watson: For any entrepreneur, your network plays a significant role in your success, though this isn't necessarily one that you inherit from your family or even from where you went to school. In my own case, being thoughtful and strategic with how I build my network and manage those relationships has played a big role in my success thus far. For just one example, all of my current investors have come from warm introductions.

Final Word

Since closing Jet.com, Squad has continued to close enterprise customers and successful shift into the consumer market. Their success, and Watson's leadership, demonstrates how powerful we can be when we focus on making an impact and combining that focus with hustle and creativity. Consider this advice, and find out how you can follow in Watson's footsteps, improve your business and create more success.

Published on: Dec 28, 2018
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