Life in Law

For a general counsel position at any major company, a continued commitment to law is generally requisite. But chance took Ironclad GC Chris Young from basketball to a key role in Barack Obama’s presidential campaign, in preparation for GC stints at two venture-backed tech upstarts.

Taking up a career in law is a full-time undertaking – of that there can be no doubt. There’s just no substitute for the commitment, both personal and professional, to pursue the pinnacle of the legal track. You’re either in or you’re out.

Or are you?

In that respect, Ironclad general counsel Chris Young is certainly the exception to the rule. Taking up law as a backup option following the disappointment of a professional athletic career that didn’t quite materialise, Young would wax and wane between the worlds of lawmaker and legal practitioner throughout his 20s and 30s – the period of time during which most wide-eyed lawyers are busy cutting their teeth at the photocopier and tailing partners in the faint hope of recognition.

But taking the well-trod path was probably never going to be an option for Young – it just isn’t in his nature. Five minutes in his company is more than enough to demonstrate that to even the most prominent traditionalists from the legal industry.

‘My journey, it certainly isn’t the usual one – nor one that that I think too many people would be in any rush to emulate,’ says Young.

‘I’ve taken a lot of chances, a lot of risks and I’m fortunate enough to have come out on the right side. Some of that has been through good old-fashioned hard work, some has been through being in the right place at the right time. But I’m not too proud to admit that a lot of it has probably just been straight-up luck!’


Despite living a career (still in its relative infancy) that would be the envy of those pursuing either law or politics (or both), neither were even on the radar for Young as he entered his final year of high school.

‘Like many 18-year-olds, I was convinced that not only was I going to get a full-ride scholarship to a [National Collegiate Athletic Association] Division I school, but that I was probably going to play in the NBA one day. It wasn’t too long after my senior year of high school that I realised my dreams in that respect, unfortunately, were probably not going to come true,’ says Young.

‘Becoming a lawyer – honestly, it wasn’t exactly my first choice. It came about when my basketball dreams didn’t materialise in the way I thought they would.’

That his basketball dreams didn’t materialise wasn’t for lack of ability or opportunity; rather, Young was a victim of circumstance and poor timing – certainly the only time those final two words grace this narrative.

‘I had received a full-ride scholarship offer to go to the University of Denver and play basketball for coach Dick Peth,’ recalls Young.

‘I decided not to sign before my senior year started, because we had such a strong basketball team that I figured other offers would come in throughout the course of my senior year. Turns out, there was no stronger offer than the initial one I received from the University of Denver.’

‘Obama’s message resonated because what he talked about was something that I’d lived.’

‘Just as I was scheduled to fly out and sign my letter of intent and meet with Coach Peth, he called me to let me know that he was moving on to a different school. The head coach position was going to be assumed by another Division I coach from the south, who would be moving up and not only taking that position, but bringing his recruits with him. The upshot was, if I hadn’t signed by that point – which I had not – I no longer had a slot.’

Through no fault of his own, Young’s dreams of starring on the hardcourt had been squandered – forcing an audible of the highest significance at the most inopportune moment. But disappointment is all about how you deal with it. And Young had the right support networks in place to help him retain a level head and chart a new path.

‘I’ll never forget the conversation my father and I had one night after that. We stayed up until the sun came up, talking about what I was going to do, what my career was going to be if I didn’t play basketball. It was that night I decided I wanted to be a lawyer,’ he says.

‘What first piqued my interest in the law was the prospect of becoming a sports agent. I figured that if I couldn’t play basketball myself, maybe I could represent basketball players – help guide them financially, legally and otherwise – and potentially make a good living myself. It seemed like a dream job, I’d still be around sports, but as a lawyer. Not a bad consolation prize to being a player myself.’


Adjusting at the last moment is rarely an easy task – let alone when the stakes are as high as deciding on a tertiary institution and, subsequently, a career. But Young would take it in his stride and, following a whirlwind tour of prospective colleges, opted to accept a place at San Diego State University.

‘When I got to college, my mind opened up much more than I could have imagined. I had a chance to take honours courses at the university and learn about things I hadn’t learned about before – I really got into the civil rights movement,’ says Young.

‘What fascinated me was not only the ability of a bunch of ordinary people to come together to do extraordinary things, but the role that the judicial system – and in particular lawyers – played in those civil rights battles. I became inspired by some of the lawyers who, throughout history, fought for and on behalf of people who didn’t have rights everyone else had and often didn’t have the voice to fight for themselves.’

Young credits his interest in civil rights, but perhaps more broadly his success during this period, to the strong mentorship he received from a number of figures who were willing to give him the benefit of their time and experience. But one in particular stands out – someone who continues to play an important role in his life to this day, nearly 20 years on.

‘For me at the time, it wasn’t just reading the literature or attending the classes that led me to be so passionate about civil rights and trying to affect change, it was actually a professor named Dr William Cheek,’ explains Young.

‘I had the privilege of taking his class when I was 20 years old. He was a white southerner from Virginia with a southern drawl. I walked in and I immediately thought, “I’m not sure this is going to work.” So I sit in the back of the class as I always did. Throughout the year I’d move up closer and closer to the front of a class based on how engaged I was with the subject matter. It only took me two weeks to sit in the front row of Dr Cheek’s class. And it only took two weeks or so after that to meet with him during office hours to get to know him.’

‘It seemed like a dream job, I’d still be around sports, but as a lawyer.’

‘Dr Cheek is a well-renowned biographer and a historian who focuses on the civil war, reconstruction, and the Jim Crow and civil rights eras. Being with him and learning more and more about our country’s rich yet disturbing history is really what heightened my newfound passion for civil rights and considering how I might one day try to affect change after earning a law degree and becoming a practising lawyer.’


As Young graduated from San Diego State with a Bachelor of Arts, with law school and the pursuit of civil rights both weighing heavily on his mind, he faced a crossroads of sorts. One, he admits, was rooted in fantasy as much as it was in reality.

‘At this time, I had this vision and this fantasy of one day working to bring people together. Bridging the divide in America, creating empathy, and doing all the magic that some of these giant legal minds and practitioners had done in this critical era of American history, the civil rights era,’ says Young.

‘I applied for law schools. I also applied to be a Senate Fellow in the California State Senate. The idea was that I always knew I had some interest in government, politics and policy.’

While a desire to pursue politics in some form was of clear interest for Young, instead, he would opt to return to Sacramento and put law school on hold – a decision in large part motivated by a desire to return home and help his family, in particular his mother, who was recently widowed following the loss of his father.

‘Instead of going straight to law school, I took a different track and before starting my fellowship in the Senate was presented with an opportunity to intern with a man named John Burton, who was a long-time, well-respected senator representing San Francisco. It was in his office that I responded to letters from prisoners who had complained that their parole date continued to get pushed, and they were being wrongfully denied their day in court, so to speak,’ says Young.

‘It became really important to me to learn about these issues, learn about the Prison Litigation Reform Act and to be responsive to the prisoners that were frustrated that they didn’t have a chance to prove they were worthy of a second chance.’


In a period where Young was laying the foundations for his future professional life, it’s prudent to consider how his past – and, in particular, that of his parents – shaped the philosophies and beliefs that would characterise this time for him.

‘My father is black, he was from just outside of South Central Los Angeles – specifically a city called Watts. He ran away from home when he was 11 years old, joined a gang, and became a well-known gang leader over the years,’ explains Young.

‘He also spent most of his adolescence and early adult life in prison. In fact, the last time he served in prison, he served in Folsom Prison, which is near Sacramento. When he paroled from prison, he decided not to go back to Los Angeles, and instead stay in Sacramento.’

That decision would be a life-changing chance for Young’s father – much like the ones which have shaped Young’s own life – eventually leading to his father and his mother meeting, as well as the chance for his father to pursue higher education himself, going on to become a married school teacher with children – a far cry from the life he left behind.

‘Despite not having spent a single day in high school, my father taught himself how to read in prison and very much wanted to get a college degree. After completing his last stint in the penitentiary, he enrolled in the Educational Opportunity Program through Sacramento City College. He rented a small studio apartment in a house, a Victorian house in downtown Sacramento, referred to as the Pease Conservatory,’ says Young.

I had this vision and this fantasy of one day working to bring people together.

‘It was at this house where people taught music too. My father was in this little studio upstairs. The second and ground floors were people teaching music. My mother was a young piano teacher, with blonde hair and blue eyes. My father admired her from afar, but he was black, had been shot in the face, had scars all over, was beat up, and fresh out of state prison. He thought, in no world, in the early 1970s, when it was still illegal in certain places in the United States to even marry someone who wasn’t your race – particularly a white woman marrying a black man – that there was any chance in hell that they would actually link up. But they did and as soul mates enjoyed a long, beautiful marriage before my father died nearly 30 years later.’


Fast forward a few years and Young would find himself facing opportunity once more. After accepting a scholarship to UC Berkeley to study law – slightly later than anticipated but not without the benefit of government experience – Young would find himself working as a litigator at Morrison & Foerster.

‘While there, I had the opportunity to join Tony West, another mentor of mine [and now general counsel at Uber], and a few others to participate in a conference call with Barack Obama. We were all early donors to his exploratory committee. On the call, Obama mentioned that he would make a decision over the holidays about whether to run for President,’ says Young.

‘Well, as we know, he did in fact decide to run and made his announcement speech in February 2007 in Springfield, Illinois. At the time, I flew out to attend his announcement speech with what’s now quite a star-studded line-up of folks: Kamala Harris, who’s herself running for President but was then district attorney of San Francisco; her brother-in-law, Tony West; now-mayor of San Francisco London Breed, before she’d ever run for office; and Ben Jealous who just ran for Governor of Maryland.’

‘This little group of us, we were all living very different lives at the time, but had the opportunity to go down to the basement of the Capitol with Obama’s close friends and family. We had the chance to meet with Barack and Michelle [Obama], exchange niceties and take pictures.’

It was at this brief gathering that Young, unbeknownst to him at the time, would leave an impression on the future President – although probably not for the reason he had hoped.

‘I had to take multiple pictures with Obama because the camera I was using kept failing to fire properly. He seemed to be getting a little annoyed with me, but I showed him what was happening and he was cool about it. From then on, he seemed to remember my name – even if it became a bit of a running joke,’ explains Young.

‘Two days later at a kick-off fundraiser in Chicago, I went up in an elevator together with both Barack and Michelle. The first thing he said to me was “Another picture?”. Every time I saw him from then on, I was always asked about whether I wanted a picture. Until one day he said to me, “So are we going to keep taking pictures or are you going to help me with this campaign?”’


While the offer from Obama was a tempting one, it wasn’t as straightforward a decision as it may have first appeared, particularly with the benefit of hindsight. Now secure in a role at Morrison & Foerster, with the prospect of clerking for a federal judge on the horizon, joining the campaign of a man then seen as having a remarkably outside shot at the presidency represented a major risk – personally, professionally and financially.

‘At this point, I hadn’t taken it too seriously. But when I gave it some thought, spoke with some of the folks at the firm, as well as the deferral district court judge I was supposed to clerk for that summer, I made up my mind,’ says Young.

‘Both the judge and a few partners at the firm really encouraged me to take a risk and go out to campaign with then Senator Obama. So I took a leave of absence from Morrison & Foerster and worked out an agreement with the judge to go back at a later date and I set off as Obama’s first hire based here in Northern California as his deputy finance director.’

While the backing of his legal contemporaries may have made the decision easier than first anticipated, Young believed in the message and timing of what Obama was campaigning on.

‘For me personally, Obama’s message resonated because what he talked about was something that I’d lived. Like him, I had a white mother and a black father – I could empathise with his situation, figuring out his identity as he grew up,’ explains Young.

‘I also appreciated the unique talent Obama had with his ability to stir the emotions of the masses and create empathy between groups that historically have been divided. In being white and being black, he could navigate between both worlds, so to speak. I also thought at the time, two years into George W. Bush’s second term, that what the country needed was unity. We needed someone who could bridge the divide and bring us together. That’s what originally attracted me to the campaign.’

‘Change doesn’t have to be effected on the macro level, it can be effected on the micro level.’

Proudly recounting war stories from the campaign trail – and what represented a near two-year commitment in his life – Young can distil the personal takeaways to a single, most prominent lesson.

‘One of the biggest lessons I took from spending as much time as I did with Obama was his ability to keep his composure. He really always, always embodied that, it didn’t matter how stressful a situation would be, all the highs and lows of the campaign, he remained composed,’ says Young.

‘I’ve often looked back on the highs and lows he faced, how he dealt with them, then used those as inspiration as I navigate my own life – both personally and professionally.’


In the years that followed the Obama campaign, Young would tread the line between both law and politics, working with Sacramento Mayor Kevin Johnson’s transition team in the immediate aftermath of his election and later his senior counsel and adviser, then as a political appointee in the US Department of Justice, before taking up a position at litigation powerhouse Keker & Van Nest [now Keker, Van Nest & Peters]. After spending four years there, he would depart to join a former colleague at the venture-backed upstart, OpenGov, an opportunity to combine his legal knowhow with his passion for politics.

‘While at OpenGov, I got a call out of nowhere from a partner at a well-known venture capital firm who asked if I had any interest in being the first lawyer at a company called GoFundMe. At the time, I was happy with my position. I hadn’t heard of GoFundMe – something I would later learn put me firmly in the minority of most Americans,’ Young explains.

‘I went in, I spoke with the folks, was impressed by the service and what the platform provides people all over the world and, of course, the team that they had assembled to take the company to the next level was incredibly impressive. I was fortunate enough to receive an offer, and I joined the company shortly after.’

At GoFundMe, Young had the opportunity to cut his teeth as an in-house counsel, while also shaping the direction of his department of one and helping to cultivate a culture that resonated with his own personal beliefs and philosophies, particularly in the area of diversity and inclusion.

‘What stood out was that GoFundMe understood that it had a very diverse userbase and so, on our executive team, there was a real premium placed on championing diversity both in terms of personnel and of perspective. For me personally, in the legal department, most of my work from a diversity and inclusion standpoint was carried out in the form of hiring diverse outside counsel, and hiring underrepresented minorities on my team. I’ve often believed that it’s good to talk about diversity, and raise the issue, and make sure it’s at the forefront of folks’ minds, but I found that even more important than talking about it is actually acting on it,’ says Young. ‘At GoFundMe, like many other companies, the legal department was viewed as a cost-centre and in-house lawyers are often expected to do more with less. Whereas I had worked at the US Department of Justice and at a private law firm where you have all the support you could possibly need, as in-house counsel I had to quickly figure out ways to build machines or to procure software that would help cut out a significant amount of the administrative work so that I could focus on the more strategic and impactful work that was expected of the company’s counsel.’

It was during this search for technological efficiency that Young would first come across Ironclad – then a small-time start-up, whose software was helping to change the face of contract management for in-house counsel.


‘Ironclad’s focus was on contract management, including by automating various contract-related processes that turned out to be pain points for me. I implemented it relatively quickly. In fact, it was the first software I procured, ever, but also at GoFundMe,’ says Young.

‘In getting to know the organisation well, I realised very quickly that every company is a contracts company and every team is a contracts team. Whether it’s HR, sales, marketing, finance, G&A, you name it – contracts are everywhere. And for any in-house counsel, manually managing contracts and not knowing where they all are or what’s in them is going to keep him or her up at night. So, I watched this company with this incredible product address a need in the market that was absolutely glaring and, over the years, watched them continue to grow and evolve. Fast forward almost three years from the time that I met Jason [Boehmig, CEO], there was an opportunity to join the company as its general counsel, and I jumped at it.’

Now six months into his tenure at Ironclad, a company that, like any start-up – even one backed by venture capital powerhouses like Accel and Sequoia – once again represents both major risk and opportunity for Young, he remains upbeat and excited about what lies on the horizon for the upstart company – after all, for a legal software company, it’s hard to have a better recommendation than an avid user coming on to join as general counsel! Faced with the prospect of once more starting from scratch and having to reinvent himself, it again becomes a matter of first principles for Young.

‘For me, the North Star has always been an insistence on spending my professional time having a positive impact on people,’ says Young.

‘One of the lessons I’ve learned throughout my career is that you can’t forget what initially motivated you to get a law degree. Although I have not become a civil rights lawyer, I’ve never forgotten why I decided to go to law school. It’s to effect change. Change doesn’t have to be effected on the macro level, it can be effected on the micro level. It doesn’t have to be the entire United States or the world. It can be a community. It can be someone you mentor. It can be personal. It can be professional. It can be a combination of all those things. So long as I don’t lose sight of that, I’m up for whatever life may throw my way.’