Leader to Leader: John Raskin

Founder’s syndrome is a common affliction in the nonprofit sector. Launching a successful nonprofit isn’t easy. Identifying a compelling problem to solve … raising money … building a team … demonstrating impact …. To overcome these kinds of challenges typically requires a leader of vision and drive. 

But there is a flip side. The same force of personality that enables a founder to persevere in the face of long odds at an organization’s inception sometimes comes back to haunt an agency in later years. Many founders effectively become victims of their own success. They find it difficult to adapt as their agency grows. They hold on to the spotlight – and to decision-making authority that should be shared with members of the staff and board of directors.

Is it possible to avoid these perils? How does a visionary nonprofit leader figurea out that it is time to step down? And how does he prepare the organization – and himself – for his departure? 

I put these questions to John Raskin, who stepped down as the executive director of the Riders Alliance last month. Raskin helped to found the organization eight years ago in an attempt to improve public transportation in New York City. The agency’s efforts to mobilize public transit riders have been credited with helping to pass congestion pricing legislation in Albany – a move that is ultimately expected to contribute hundreds of millions each year toward improving the transit system. Riders Alliance also played a critical role in mobilizing support for Fair Fares, a city initiative to introduce discounted MetroCards for low-income New Yorkers. On the heels of these achievements, Raskin announced his resignation.

I spoke with John by phone. This transcript has been lightly edited for length and clarity.

Berman: So tell me, your last official day at Riders Alliance was when?

Raskin: March 6th.

Berman: How does it feel to step down at this precise moment in history?

Raskin: Look, more than anything, I think I have a little bit of guilt. My successor, Betsy Plum, is doing a great job running the organization, but this is a crazy time for someone to take over a not-for-profit organization. Our work has to adapt so radically. She is having to reinvent all of our procedures and systems and methods of working within the first couple of weeks on the job. Kudos to her and to our team for being adaptable and thriving as much as anyone can in this time.

Berman: But that's Betsy's experience. What about your experience?

Raskin: In this crazy time, I feel like I'm at my full capacity just trying to manage our baby and taking care of life at home. I can't imagine also having executive responsibility for a not-for-profit organization at the same time. I don't understand how anybody's getting anything done, but they are.

Berman: Do you have a feel for what kind of impact the coronavirus crisis is going to have over the long haul for the city's transit system?

Raskin: Long term, we just don't know what impact the virus is going to have on public transit. I think short term, there's a huge financial crunch. Part of the work at the Riders Alliance over the last month has been to guarantee that public transit is part of the conversation as government looks to bail out different industries. I think all the private industries have their well-connected lobbyists who are able to make the case for why they need public money. Part of what we provide is we turn public transit riders into their own lobbyists. And so we've had to kind of figure out how to do the organizing virtually, which is different from anything we'd ever done before.

Berman: Rewind for me to the founding of Riders Alliance in 2012. What was the original vision and how were you positioning the agency within the ecosystem of other nonprofits working on transportation issues?

Raskin: New York has many longstanding organizations that do extraordinary work on public transit, including Straphangers and Tri-State Transportation Campaign and Regional Plan Association and Transportation Alternatives … the list goes on and on. Those of us who worked to create the Riders Alliance all had experience working in local politics in one way or another, and we saw that the issues that got attention from elected officials were issues that had a constituency in the community that was organized to make demands on their legislators and to hold them accountable for the outcome. That was different from the advocacy work that was happening in public transit, which was focused on communications and policy work and direct lobbying. There are eight million people a day who take the subway and bus in New York City. That was a huge under-tapped source of power. We thought that if you could organize even a small portion of the millions of people a day who rely on public transit in New York, you could really add some energy and juice to the movement for public transportation, and that's what we set out to do. But we were very conscious from the beginning of making sure that we were not duplicating others' work and that we were providing something that added value.

Berman: You made reference to the eight million public transit riders … it is impossible for any organization to claim that they represent all of these people. How many members do you need to have in order to feel like you can speak with some authority on behalf of riders?

Raskin: It's a moving target. If you're organizing around improving G train service in North Brooklyn and Western Queens, then you don't need to have thousands of people. There are a relatively small number of people who can sufficiently claim that they are G train riders and can make demands on the MTA and their elected officials on behalf of G train riders. For that reason, we chose small fights when we started out. When we started out in 2012, the campaigns that we took on at the start were to improve G train service, to restore a bus line in Brooklyn that had been cut and had been popular in the community, and to add service to certain buses in parts of Queens. These are hyper-local fights, and they're not going to change millions of people's lives, but they were appropriate for the strength that we had at the time. This is the ethos of community organizing: Start with a fight that you can win with the power that you have, and then use that fight to become more powerful for the next time. That's kind of textbook community organizing, and that was our approach. We did win more G train service. And by winning this relatively small fight, we also built a membership base, we built a reputation, and we built relationships with the news media and elected officials. And from that, we were able to move on to bigger fights. The trajectory of the organization over the last eight years has been taking on successively bigger fights, culminating with the effort to win congestion pricing.

Berman: As you look backwards, to what extent did the trajectory of the organization conform to the plans you had created and to what extent did it depart from what you originally anticipated?

Raskin: Many organizations that had come before us had mapped out the basic idea that you build from small wins and take on bigger fights. We didn't actually have a sense at the outset of what those bigger fights would be. That's something where we really had to keep our eyes open and be alert for opportunities as they came up. In many respects, the Riders Alliance grew out of the loss of the congestion pricing fight in 2007-2008. That experience made it clear to me and the other folks who put together the organization that many elected officials were not being responsive to the needs of their transit-riding constituents. And so I think we were always interested in revisiting the congestion pricing fight, but we would never have been able to tell you in 2012 that we were going to do it. For nonprofit organizations like ours, success is often a combination of doing the work and then being ready for the moment when it comes.

Berman: Were you from the start thinking about creating an organization that was going to outlive you?

Raskin: Yeah, absolutely. It was always part of the plan. The ethos of community organizing is that you don't build an organization as a vehicle for any one person or one group of people. You build an organization because there's a constituency that would benefit from being organized. A core value of community organizing is to try to organize yourself out of a job – to build leadership among both staff and grassroots members so that the organization is really strong and any one person can depart and leave the organization stronger than when they came.

Berman: You've made reference several times to the tenets of community organizing. Do you have formal training in organizing?

Raskin: My training in organizing is almost entirely experiential. I came of age professionally with a neighborhood group in Hell's Kitchen called Housing Conservation Coordinators. I was hired as a community organizer and dropped into the community fight to oppose the West Side Stadium that Mayor Bloomberg wanted to build.

Berman: That’s funny – I have friends that were on the other side of that fight.

Raskin: Actually a lot of my friends were on the other side of the fight as well. I think that's just a testament to how politics work in New York: People you're fighting with one day can become your close allies in whatever the next fight is. That's certainly how it's worked out for me.

Berman: Were there things that you consciously put in place in the early years of Riders Alliance that you think have been crucial to ensuring the longevity of the organization?

Raskin: I think so, although I would say there was not a master plan to build that sort of capacity. I certainly didn't have the vision at the outset for how to achieve it. I think in the early years at the Riders Alliance, the organization was very strongly identified with me personally as the executive director. But I think that shifted as time went on. We really did develop staff members and grassroots leaders who had on-the-ground expertise and the ability to speak with press and to work with elected officials. And so some of the attention of the organization shifted away from me in a way that was organic. We also deliberately worked to build a stronger board. We have for many years been a partner project of the Fund for the City of New York. And so for legal purposes, our board has actually been an advisory board, not a legal governing board. But we treated the board like a legal fiduciary board even if it didn't technically have that responsibility. I also credit our development director, Sonia Isard, who played a leadership role working closely with board members and with me to make it happen. If I’m honest, building institutional infrastructure was not my personal strength. I think there's a degree of luck involved in having some co-leaders of the organization who were really thinking in those terms and able to take the steps to make that happen.

Berman: Many leaders want to leave on a high note, and the congestion pricing victory certainly provides that. Were there internal milestones that you were also looking to achieve before you were ready to step down? Were there signs that signaled that the organization was now ready to outlive you?

Raskin: I'm sure there's a master-class executive director who could give you a rubric of how to evaluate when it's time to leave. It was never so specific or concrete for me. Part of what prompted it was the policy work of the organization. Having a couple of significant victories like Fair Fares at the city level and congestion pricing at the state level made me realize that the Riders Alliance was concluding a natural cycle of the organization's work. To be healthy, the organization would now have to embark on a new cycle to figure out what the new opportunities are, and how are we going to do organizing for the next five or 10 years. It felt like the person who was going to lead that thought process really should be someone who's going to be there for five or 10 years and it just didn’t feel right for me personally to make a renewed commitment of another five or 10 years.

I think that I also felt comfortable leaving at this time because we have the structures in place that could help with the transition to a new executive director, and by that I mean we have a really strong, engaged board, we have some very strong leadership on the staff, and some very strong donors. The Riders Alliance is funded largely by individual donors and by foundation grants. We have developed some pretty deep relationships with funders, and we're in a pretty good financial condition.

Berman: Tell me about the selection of your successor, and what role, if any, you had in that process.

Raskin: Our board chair, Michael Freedman-Schnapp, led the process. The search committee had members of the board and staff on it, and was supported by an executive search firm – Koya Leadership Partners.

Berman: So you played no formal role?

Raskin: I think it would've been unrealistic to have me play no role, but we wanted to be very deliberate about the role I'd play. I didn’t want to crowd out other voices. So I was not on the executive search committee and I was not in the interviews with the search committee. But once they selected finalists for the position, I did sit down with each of the finalists to have a conversation. That was both informational for the candidates and it also gave me the chance to talk with the candidates personally and get a sense of what they would bring.

Berman: Were there one or two skills that you thought were particular priorities?

Raskin: I think everyone agreed that we needed someone who shared our core values, and understood the value of community organizing. And everyone agreed we needed someone who would be comfortable going out as a front person and being in public and pitching elected officials, donors and members of the news media. So, I think that those were shared priorities. As we went through the search process, something that I tried to push for was that we needed someone who had very strong strategic sense from an advocacy and organizing perspective.

Berman: What do you mean by that?

Raskin: With some nonprofits, if you're not really sharp about what issues you take on, or what goals you set, you may be less efficient or less effective, but you will still get something done. With a community-organizing group like Riders Alliance, if you don't choose the right issues and you're not sharp about how to achieve your goals, you literally accomplish nothing at all. The New York political system and the news media is so fast moving and it's so challenging to make progress and stay relevant in the discussion around the state budget or whatever the issue of the day is that you need a leader who has a discerning enough eye to understand when an organization is making a difference and when it's not. 

Berman: After the selection process, you agreed to overlap with Betsy, correct? What was the timing?

Raskin: We announced publicly my plan to depart in July of 2019. So the search process began in July and took five months or so. We hired Betsy right around New Year's. Betsy had significant responsibilities at the New York Immigration Coalition that she had to wrap up, so she formally began with us in mid-February. I stayed for three weeks of overlap, just to give Betsy a sense of the weekly rhythm of the organization and how we do our work. The day Betsy showed up, she sat at what had been my desk in the corner of the office. I moved to what had been the intern desk. We tried to be very conscious. It was a process of my letting go and also the staff and board letting go of me in the role. It helped that everyone was very excited about Betsy coming on and that both the staff and board were confident that we had made a great choice. It also helped that we had a long time to prepare for it, and started some of the transition, both logistical and emotional, months before it really happened.

Berman: So, this brings me full circle because I want to return to your emotions. You artfully dodged my question earlier, but I’ll try again: How does it feel to step down? 

Raskin: It's been eight years since I co-founded the organization. And the executive transition itself, including all the behind-the-scenes conversations, had been going on for significantly more than a year. So I think over the course of that time, I really came to grips with the fact that we were choosing someone new to run the organization. Part of that is strategic and logistical, but there's an element that's very personal too. I shifted my own identity over a period of time. I used to define success as: Are we doing organizing well? Are we winning the public conversation? Are we winning the policy issues? Over the past year, the definition of success for me became: Have I left the organization in good shape and has the staff, and board and donors coalesced around the new leader?

Berman: What comes next for you?

Raskin: The pat answer is that I don't know. I had wanted to take a little break before jumping into the next endeavor. That was supposed to be a week in Puerto Rico with my husband, and has instead become five weeks of quarantine in the apartment and counting. It’s not exactly the little professional hiatus that I was looking for, but I think that the entire world is scrambling to adjust their expectations and that's true for me as well.