After a 40-year decline, entrepreneurship is having a moment. The pandemic unleashed a massive set of shifts in the way people work, and pushed some would-be entrepreneurs to take the leap.
This is only good news to Asheesh Advani, the CEO of JA (Junior Achievement) Worldwide, the 103-year-old iconic NGO that teaches millions of young people about entrepreneurship, work readiness, and financial health. Earlier this year JA was nominated for the Nobel Peace Prize and, for four years running, has been ranked among the world’s top-ten social-good organizations. JA Worldwide was also just listed among the top-100 Fast Company Best Workplaces for Innovators list.
In September, JA Worldwide will participate in the UN General Assembly and Transforming Education Summit, which seeks to reimagine education systems and revitalize global efforts to achieve Global Goal 4.
Asheesh took over the helm of JA in 2015 after building and selling two innovative companies. He founded CircleLending, a pioneer in peer-to-peer lending, which was acquired by Virgin in 2007. He subsequently served as CEO of Covestor, which blazed an early trail in online asset management and was acquired by Interactive Brokers in 2015.
I sat down to speak with Asheesh about entrepreneurial mindset, lateral leadership, building a global culture, and more.
Alisa: Asheesh, you’re an entrepreneur. What made you interested in leading a large, global NGO?
Asheesh: Great question! My entrepreneurial ambitions began when I was a teenage JA student in Toronto. I had early experiences with entrepreneurship through JA, and then went on to start a company in my twenties that ended up being acquired by Richard Branson’s Virgin Group. That experience at a young age led me to additional ventures and cemented by self-belief that I would approach each leadership opportunity as an entrepreneur would.
But then a friend in my circle lost his father. It was the first time any of my friends lost a parent, and it had a big impact on me. During the funeral, I heard stories about his life and began to dwell on the idea of impact and legacy. That was the moment I started to consider the impact of entrepreneurship and leadership in a new way.
When the opportunity to lead JA was presented to me, I was attracted by JA’s mission: To inspire and prepare young people to succeed in the global economy, to develop the next generation of entrepreneurs. I saw a chance to not only impact young people but to effect real change in the world through their work and their legacy. Gen Z doesn’t just want to start businesses; they want to improve the world, whether by rethinking agriculture in parts of the world affected by drought, breathing new life into materials that would otherwise go into landfills, building solutions to mental-health challenges, and more.
I also recognized that I’d have to learn new leadership skills since JA is global and very decentralized in its structure.
Alisa: How do you approach leading this distributed, global organization? You don’t have the same direct authority as you did in the companies you ran.
Asheesh: That’s right. JA is organized into a network of teams with more than 300 legal entities around the world employing over 2,700 individuals. We also have small teams on the ground in over 100 countries. Each team reports to a local board of directors, with additional oversight from regional and global teams. This model of distributed governance was new for me when I started at JA, but now I think it’s the way of the future. It provides the best of global, regional, and local expertise and decision-making. The idea that an executive in Boston would know what’s best for a staff member, student, or teacher in Lima, Lagos, or Ludhiana is outdated.
Alisa: That makes sense, but how do you make sure that the larger entity can align across borders?
Asheesh: We do need to coordinate on matters such as our brand, technology, impact measurement, and other elements of governance. So we introduced a framework called Fixed-Flexible-Freestyle (FFF), whereby some matters are globally fixed, regionally flexible, or local freestyle. This provides some simple language and structure to communicate what we share across borders and empowers local staff to make most decisions. For example, we recently modernized the JA brand and have been able to roll it out globally with the benefit of fixed, flexible, and freestyle parameters so there is some clear commonality but also significant local control on how it comes life to benefit local schools, students, staff, and funders.
Alisa: But how do you get people to do what you want them to do?
Asheesh: Well, I seldom do! Instead, we try to co-create solutions with the JA network. For example, we have an initiative called JA Labs, in which we define a theme—say, “solutions for empowering the underserved”—and provide funding to JA locations which apply to either expand a small pilot or try something entirely new. We’re not as concerned about an initiative failing as we are about not trying in the first place.
Alisa: I have been reading and talking to people about Web 3 and decentralization—both as a technology and also as an organizing structure. And we’ve heard a lot about DAOs (Decentralized Autonomous Organizations) requiring a new form of leadership. It sounds like JA has some similarities to DAOs.
Asheesh: JA reaches more young entrepreneurs than any other organization on the planet. And I can tell you from meeting these dynamic trailblazers that they understand and embrace decentralized leadership more readily than successful business leaders who are over the age of 30.
Web 3 leadership requires an understanding of decentralization that is modern and different. It’s not only about accepting that others have a different viewpoint than yours or about building diverse teams, but also about welcoming that difference and inviting others to raise their hands to co-create and co-organize the initiative, even if the outcome is different than what you wanted to achieve. Some leaders have a hard time losing control of the outcome—I’m not immune to this myself—but in the end, I find that the outcomes exceed my expectations rather than falling short of them.
Alisa: If you can’t control the outcome, how can you manage the expectations of board members and investors?
Asheesh: That’s exactly why leaders may have a tough time embracing lateral leadership and decentralization. Managing expectations is core to what most leaders have to do, but we have yet to figure out how to effectively communicate to board members that short-term outcomes are less important than long-term impact. Leaders need to do both: delivering short-term outcomes that are measurable and clear builds social capital with board members and investors. That allows them to then embrace longer-term initiatives that allow for investments in the vision, the change you want to see, and impact, our role in bringing that change to life. That’s tough to do in practice.
Alisa: What else keeps you up at night?
Asheesh: In the near-term, it’s the learning loss caused by the pandemic. (That, and my twins’ college applications, which are due in the few weeks!) Longer-term, I’m concerned about global issues that are best solved locally, but perhaps aren’t on a timeline that’s fast enough to make a global impact, or don’t have the funding that global scale could bring. This is especially true of tech solutions.
There’s so much we can do with technology that can make a real difference around the world—especially in the context of education—but some of those solutions won’t accommodate the millions of young people without access to the broadband or devices they need to participate. We’ve made both sides of the ed-tech equation (the proliferation of it and the need for lower-tech options) central to our strategic plan, but it’s still keeping me up at night.