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Alumni Spotlight: Jonathan Truppman

October 14, 2021

Alumnus Jonathan Truppman, General Counsel and Corporate Secretary, Casper, practiced in the firm’s Litigation Department from 2010 to 2012 and 2013 to 2015.

Paul, Weiss: What brought you to Casper?

Jonathan Truppman: As fate would have it, a weekend in the Hamptons with friends. I met Philip Krim, one of the founders of Casper, while lounging at the pool reading Anna Karenina. I didn’t exactly blend in, which led to some intellectual banter that sparked a connection. Shortly after founding Casper in April 2014, Philip called me up and asked whether I had any interest in joining the company; I declined, joking that I was “taking my talents [back] to South Beach.” At that point, joining a start-up wasn’t really in the cards. I was at Paul, Weiss, waiting to start a clerkship with the Hon. Adalberto Jordan on the Eleventh Circuit. As a Miami native, I was planning to move home to get more civically involved in the community. Like all good CEOs, Philip didn’t take no for an answer and took me to lunch around the corner from Paul, Weiss at the Modern.

During our initial meeting, he pitched his vision for building the world’s first holistic sleep company. It admittedly piqued my interest, sounding bold and prescient, so I agreed to meet with Casper’s co-founders. I quickly recognized that this group of very smart, quirky founders was onto something; from the outset it was obvious how passionate they were about creating a brand to help people sleep better.

After that, I decided to dig in and solicit advice from rabbis, mentors and psychics alike. Some people thought I was crazy to consider leaving Paul, Weiss and give up an Eleventh Circuit clerkship to “sell mattresses,” but I decided that with no wife and kids, if there was ever a time to roll the dice and take a leap (to sleep), it was now.

PW: What was the transition like from Paul, Weiss to a small start-up?

Jonathan Truppman: When joining a young company, the first thing you should do is quickly figure out how you can be helpful and make an impact. There are no swim lanes at an early-stage company of that size—it’s all about rolling up your sleeves, shedding any semblance of ego and getting to work. Coming from the structured world of a law firm, it was an exciting shock to the system, both invigorating and challenging.

I also found that you need to forget about job titles or expertise and embrace the unknown. Most of the responsibilities, especially in the early days, are going to be in areas that you have no business being in. Early on, you realize that it’s not about whether you know how to do something, but about speed and how many phone calls away you are from finding the right answer, or the right person to help you.

This is where your network is crucial. The connections you make—during your time at Paul, Weiss, in law school and in your social circles before and after being a lawyer—are going to be the people you rely on to increase your effectiveness by broadening and deepening your reach. This is always my advice for young lawyers.

PW: What is your day-to-day like as General Counsel and Corporate Secretary at Casper?

Jonathan Truppman: As a team builder and executive, you have various responsibilities to deal with day-to-day: securities filings, intellectual property, human resources issues and more, not to mention the infinite fire drills. You must ruthlessly and constantly prioritize in accordance with the company’s priorities. I know it sounds cliché, but in my opinion, the number one priority—and priorities two and three as well—as an organization grows from a small, founder-driven company to a public company, is culture.

The sense of community and the close-knit nature of employees at a small start-up tend to cultivate clear values that spread throughout the organization. As companies grow, it is critical to reinforce those values by developing consistent ways to communicate the mission, vision and values of the company, as well as its commercial priorities.
Instead of being an inhibitor, the legal team is a cross-functional lynchpin responsible for empowering the business while also helping everyone sleep at night. Given this, it’s important for the legal team to spend time with the commercial teams on a day-to-day basis. When I hire specialists, their immediate priority is understanding the entire business holistically—from product development to tech and everything in between—to ensure that they and the rest of my team can more effectively work with and support the commercial teams.

PW: The timing of Casper’s IPO took place just about a month before COVID-19 hit the U.S. in full force. What was it like helping to launch the IPO? How has your focus evolved amid the pandemic?

Jonathan Truppman: Casper is one of the first digitally-native multichannel consumer companies to go public. We were founded as a customer-first company, and as the world has changed we have continued to evolve, always identifying shifting needs and innovating or evolving the brand to meet our consumers where they are, whether that is at a Casper Sleep Shop, at essential retailers like Target or Costco, or through e-commerce and social media. The pandemic showcased the benefit of the company being channel-agnostic—we were able to pivot when people started spending more time at home, online, and most importantly, in their bedrooms.

When it comes to the IPO, I think companies have to make a decision: they can either bring someone in that has done the IPO process a thousand times, or they can decide, like Casper did, that someone like me knows the company best. Once again, this is where your network is critical—I hit the pavement to solicit advice, probably having coffee or calls with 75 general counsel and others who had gone through the IPO process.

As the general counsel and corporate guardian, you have a unique aerial view of the business—combining that perspective with executive presence and professional relationships is key to running an effective process. As part of a rapid-growth company, you are frequently learning something for the first time, and then hiring someone that can do the job even better than you, fusing historical knowledge with subject-matter expertise. For example, when I hired outside counsel, I listened and learned as much as possible from the experts. Once I had the foundational knowledge, the process was actually rather mechanical.

In this type of environment, learning to delegate is essential. As a type-A person who was successful at Paul, Weiss, I had to learn how to let go and say, “my time is better spent focusing on the big picture instead of dotting every ‘I’ and crossing every ‘T.’”

PW: What do you see as your biggest professional challenge in a post-pandemic landscape?

Jonathan Truppman: The pandemic has and will continue to change how we work in the future. Against this backdrop, cultivating company culture and building a strong team spirit is more important than ever.

On an individual level, it has always been and will continue to be about balancing the short- and long-term goals. As a GC, you could spend your entire day—and night— blocking and tackling with every crisis that comes up. If I did that, I would never spend any time on what is important to help the company achieve its long-term goals, or my own long-term goals and growth. I block time every week on my calendar, titled “worst things first.” It reminds and pushes me to do the worst things first, which sometimes means figuring out who can do them better, pivoting afterwards to focus on the gratifying work that drives the company forward.

Beyond making time, it’s important to identify and address your weaknesses, which doesn’t mean eliminating them. The worst things are different for everyone; try to hire people that enthusiastically excel where you struggle. Not only will it make you happier, but most importantly, the job will get done better. There’s no room for ego.

PW: What advice would you give someone who is interested in a similar career shift?

Jonathan Truppman: It is important to think holistically about your value-add as a lawyer. For example, clients certainly need somebody to write an exceptional brief—it is a critical task—but there are plenty of talented brief writers out there and even more in the pipeline.

To be successful, it is also important to leave your office. Prioritize forging relationships and building credibility and trust. Saying yes, keeping your head down, and just doing the work is not going to do you any favors in the long run. Businesses want people who have integrity, challenge assumptions and sometimes say no. Do people trust your judgement? Do you bring something beyond basic legal skills to the table? Just being a workhorse won’t distinguish you; the only reward for winning the pie-eating contest is more pie. Hard work is table stakes, but you have to make sure you are investing in professional and personal experiences that increase your value in the long run.

PW: Who were some mentors who inspired you? How have they impacted your work and relationships today?

Jonathan Truppman: A common thread across all my mentors is integrity.

At Paul, Weiss I had a number of mentors, but Les Fagen was probably the closest. I TA’ed the Trial Advocacy course he taught with Susanna Buergel at Columbia Law School and assisted with mock trials at SDNY. In addition, I worked on a number of his matters ranging from small, discrete personal representations to larger cases for Viacom and The Huffington Post.

Beyond legal excellence, he taught me how to communicate with people. With Les, the truth was never fancy, and it was always straight. Whether it was an anecdote about Judge Simon H. Rifkind storing exhibits in Florida orange cardboard boxes or his frequent reminders to never sweep anything under the rug, Les taught me to be acutely aware that you only lose your credibility once. Always wear the white hat and always be on the side of truth and justice, he told me.

Additionally, I clerked for the Honorable Victor Marrero in the Southern District of New York, who continues to be a mentor and one of the most compassionate and thoughtful individuals I have ever met. With a storied career in public service, Judge Marrero taught me to always be steeped in the law, but not to let your own legalese blind you to common sense and justice. I will always remember that once, after going down a bit of a rhetorical rabbit hole in my analysis, the judge paused, smiled and said, “Jonathan, when all legal tests fail, try the New York Post test: what would this look like on the front page?” Suffice it to say, I rewrote everything. It didn’t ultimately change the legal outcome, but the tone was much more balanced and humane. Writing concise and compelling legal arguments is necessary, but arguments are never sufficient when divorced from purpose.

On a more personal level, my late grandfather, Eli Matalon, has always been a moral compass and north star. As one of 11 siblings, he rose from poverty to become mayor of Kingston, Jamaica—the island, not Queens—and served as minister of education and minister of national security and justice under former Prime Minister Michael Manley. My grandfather instilled in me the importance of family and collective perseverance—he and his siblings went to school in shifts due to a lack of shoes, and later built a family business through shared sacrifice. Nicknamed “the Sheriff,” he constantly reinforced the importance of integrity in everything you do, large or small, through his many refrains: “Your word is your bond,” “A liar and a thief is one and the same,” or “You only lose your reputation once.”

PW: How did Paul, Weiss help you get to where you are today? What advice would you give to current associates about making the most of their time at the firm?

Jonathan Truppman: As we just discussed, mentors play a critical role, providing structure and guidance to help young lawyers build their professional foundations and ethical backbones. Make sure you dedicate time to forging relationships and cultivating mentors—this applies to both partners and associates. Seek out people you want to work with and assignments that are professionally accretive.

Most importantly, take on pro bono work. Don’t wait to “find the time”—be proactive and make the time. As a retired partner told me during my interview, pro bono is not about “getting your training wheels, it is your ethical obligation as a lawyer.” At Paul, Weiss, it is also some of the most meaningful and rewarding work you may find in your career, period.

Just as important as making the most of your time at Paul, Weiss, also make sure to maintain your relationships outside the firm, from high school, college, extracurriculars, wherever. I ended up at Casper not because of a well-planned professional path or partner referral, but because of friendships I fostered outside of the legal world. Your friends are incredibly smart individuals who go out into the world and do amazing things. This is the most important network one can foster.

PW: What is one word that best describes your outlook for 2021? What excites you the most?

Jonathan Truppman: Space. The mental space to not be inundated with noise, cable news and constantly refreshing fivethirtyeight.com for election results. If we don’t create openings for ourselves, it is impossible to grow or pursue opportunities. I am also looking forward to creating the space to remember and refocus on what is important to me—vocation and dedication rather than occupation—and figuring out how to manifest those values in both my professional and personal lives.

As Casper matures as a company, it’s about spending more time furthering our core values. For six years, we have been on a treadmill. Now, it’s about refining processes, ensuring that we are expressing our values in all aspects of the business and in everything we do at Casper. We recently hired a new chief people officer who is also our chief diversity officer, and we are looking at our organizational integrity, whether that be through diversity, equity and inclusion, or ESG, to determine our commercial priorities and implement new processes to achieve them. We could also all use some more restful sleep after the past few years.

On the personal side, it’s about moving back to South Florida, putting down roots and contributing to a community. I recently joined the board of Artists in Residence in the Everglades (“AIRIE”) and am looking forward to getting more involved, particularly as we work with our National Advisory Committee to provide a platform for historically marginalized voices in the climate change conversation and host our inaugural environmental justice summit.

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