My Pathway

I’m occasionally asked about my path in-house and, specifically, how I became general counsel of a fairly successful startup. The short answer is:

I’m living proof that the sun truly does shine on a dog’s ass sometimes.

For real.

There are plenty of lawyers who are more talented, harder working, and better suited to life in-house or as a general counsel. I very much recognize that I’ve enjoyed a semi-charmed career. This dog has seen some sun!

But I also need to be honest with myself in acknowledging that I’ve done *some* things well. And so, for the benefit of others seeking their own path, I’ve unpacked a few themes and characteristics that have served me well.

Cultivate your “why?”

I’ve heard legions of lawyers talk about how much they want to go in-house to get away from the billable hour, or unreasonable client expectations, or business-development pressures, or *any* other factor that makes practicing law, well, hard.

Newsflash: in-house life ain’t exactly a cakewalk either. But more importantly, I think you’re setting yourself up for failure if you’re choosing this path to escape something else about the practice of law. To those people I’d say, better to deal with the root cause of your troubles first.

Simon Sinek writes and talks about the importance of starting with “why?” when setting a goal. I think this has been true in my career. Before going in-house, I was a government lawyer for a few years, an enforcement lawyer to be precise. Going from enforcement lawyer to in-house lawyer is certainly unorthodox. So the question is, how the he’ll did I ever convince anybody it was a sensible move?

The answer is, I developed a compelling “why” for myself. I had the good fortune of working at the Consumer Financial Protection Bureau during the first three years of its existence. In that time, we were all busy building the organization, processes, and systems. And I learned that I very much enjoyed the building process, maybe even more than the practice of law itself.

I also learned the natural limits of enforcement work. In an enforcement action, one reconstructs what went wrong on a post hoc basis. In a successful action, financial restitution can be achieved. But it often cannot undo the harm inflicted on all consumers, or the reputational damage done to a company, or the market anxiety that sometimes follows. So, I reasoned, better to work constructively a priori so as to avoid problems in the first place. I became convinced that I might have greater positive impact on consumers and markets by working constructively with a team of like-minded, mission-oriented business folks.

Mind you, this wasn’t just an elevator pitch I developed. This became my sincere mindset. I felt it in my bones. So when it came time to convince others of my commitment and ability, my self-advocacy and “elevator pitches” were natural and compelling.

N.Y.A.O.

During an old stand up rotating, Chris Rock said the truest thing ever about how most people land a job: “You can’t get your friend a job? Shit, 99% of the people in this room got their job… because a friend recommended them.”

It’s certainly been true throughout my career. My first job out of law school *might* have been the only one that didn’t involve any personal reference or recommendation. And I emphasize “might” because, in all honesty, I forget exactly how I landed that first job.

Certainly every job I’ve had since involved some kind of intervention from a colleague or friend. My path to becoming general counsel was largely facilitated by a longtime friend and mentor who I’ll call “Bill.” I had moved back to the Bay Area after a stint in DC, and I invited Bill to lunch for I reason but to catch up on our personal lives. Over lunch, I described my experience at CFPB and how it had shaped my views about going in-house. Days later, Bill offered to connect me with a group of investors he had met who were starting a mission-oriented company in the consumer credit space, and off we went. I’ll forever be appreciative of Bill for making the introduction. He certainly didn’t have to but, as he says, wanted to help me. Chris Rock is right: many people have their job because a friend recommended them.

And we shouldn’t feel icky about this. Employers prefer hiring a known quantity over someone with an unproven track record.

What does this mean for you? Network your ass off, or, N.Y.A.O.

But do it the right way. Too many young law students and lawyers take a greedy shotgun approach to networking where they seek unreasonable favors from folks only when they need something. Or they’ll ask to “pick your brain” over coffee or lunch. Don’t be that person. It sounds greedy and inconsiderate, like you’re picking meat off a rotisserie chicken. (I know this seems like harsh advice, and I’ve been guilty of these foibles myself. Be better than I was and avoid these traps in the first place.)

Focus on building **long-term** personal relationships. This should not be a transactional exercise. Also, look for ways of adding value before taking. Even as a law student or young lawyers, you can add value to a relationship by offering to volunteer your time, write an article, organize an event, or make an introduction. Don’t underestimate what you have to offer.

Lastly, use a system to operationalize your **long-term** relationship building. No, this doesn’t mean that your relationships are transactional. It *does* mean you should assiduously track your conversations and set reminders to followup with folks so that your relationships stay fresh and vibrant. You can use a personal relationship management tool like Cloze, you can use a spreadsheet, or you can use any other system that makes sense for you. The point is, use something that helps you maintain an orderly system.

Risk/Reward

In 2014, I became general counsel of a fintech company largely because of my background and experience with the CFPB. And I got my job at the CFPB largely because of my background and experience with the Consumer Law Section of the California Attorney General’s Office. I joined the AGO from a very cushy and well paying (albeit demanding) position at a major U.S. law firm. The move involved a 50% pay cut.

You read that correctly: I made 50% less at the AGO I than I did at the law firm.

And it was painful. At that point in my life, I still owed over $100k in law school debt, and I had very modest savings. Still, it was one of the best career moves of my life because it unlocked a chain of opportunities that brought me to current day. But I had no guarantee or way of knowing that my career would work out the way it has. By leaving my law firm for the AGO, I took a legitimate risk, financial and otherwise.

I often encourage people to think of government service both because of the social good that it presents, and also because of the opportunity it provides lawyers to take on more primary responsibility earlier in their career. Yet, in my experience, law firm associates often scoff if the idea of taking such a massive pay cut. To them, the thought of making less than $80k is laughable.

It’s fine if government service isn’t for you — that’s not the point I’m trying to make. The point is, reward truly does follow risk. You should get clear on the risks you’re willing to take to achieve your objectives. Are you willing to work 3,000 hours a year? Take a 50% pay cut? Relocate? Retool you’re skills? Take a step down? What pain are you willing to accept?

I dispense all of this advice very reluctantly because I truly believe that most eventually find their way. Please consider these thoughts in the spirit in which I intend them: as friendly, constructive suggestions. Take what makes sense to you and trash the rest.

And go out there and make it happen!

Summary

1. Cultivate your “why?”

  • Clearly and honestly articulate for yourself and others *why* you want to go in-house
  • Identify specific experiences that have informed your “why”

2. N.Y.A.O.

  • Dig your well before you’re thirsty
  • Add value without expectation
  • Use a system

3. Risk/Reward

  • Get clear on the sacrifices you’re willing to make to get what you want

Goals Before 40

I recently entered the last year of my 30s and my wife asked what goals I have before turning 40. As an initial matter, I felt flattered that she’d assume I had goals at all. Rudderless suits me just fine, frankly. But rudderless at 39 seems less flattering than at 19.

So my two goals:

  • Become a level-one certified sommelier.
  • Complete one sprint-distance triathlon.

Diametrically opposed goals, I know. But I can’t think of a better way to say goodbye to my third decade.

Bursts of Thought

I’ve long admired Seth Godin and his prolific works. His short bursts of thought belie their profundity. I’ve often wished I could be more like Seth.

So I’ve decided to do less wishing and more doing. Now.

Good habits

For most of my adult life, I’ve had two habits in a perpetually conflicting loop of affirmation and decline: fitness and writing. Every quarter or so, I commit to exercising more and writing more. And sometimes those brainwaves cross, leading me to moments like now, where I find myself writing this, but not exercising, at the gym.

Both have been important to me throughout my life. In high school, I ran speed chute drills for fun. I also wrote nonsensical entries on my now-defunct Geocities page. In my early 20s, shortly after moving to LA, I joined a marathon-training group that required religious devotion to Saturday 6am runs for a six-month period, an astonishing and arguably pitiful habit for any 23-year-old with an aspiring Friday-night social life. I tried compensating Saturday nights with one stone for two birds: through a blog about local bars and cocktail culture. And then in my 30s, I participated in the Lifecycle ride from San Francisco to Los Angeles, a seven-day bicycle ride down California’s coast and farmlands. Then I became a father and most all else fell by the wayside.

But I wish it hadn’t. Because both corporeal and mental faculties, it seems, tend to atrophy with inactivity. So about that treadmill…

Interviewing Tips

I was fifteen years old when I had my very first, honest-to-Buddha job interview. It was with the City of Oxnard’s Parks and Recreation Department, which needed more scorekeepers for its adult slow pitch softball league. The interview was in a large conference room in the main city office building. I wore chinos and a green polo, the same chinos and green polo I wore to church or parties. (My wardrobe otherwise consisted of frayed jeans and tee shirts.)

My interviewers — there were two — sat next to each other on the opposite end of the table from me, holding copies of my three-page application, which included a one-page high-school caliber resume. They took turns asking me random questions off of my resume before moving on to a more impromptu portion of the interview.

“Have you ever worked before?”

Obviously not.

“Why do you want to be a scorekeeper?”

Does anybody really?

“What’s your favorite subject in school?”

Finally, a real question I could honestly answer with a lie: “Geometry.” It was actually English, but I figured Geometry would somehow make me seem more capable of keeping score at a softball game.

Why do you want the job?

This is perhaps the most fundamental question that you’ll need to answer at some point during each interview. Even if you’re not asked the question directly, rest assured that your interviewer will want to know your motivation for seeking employment with them, so do everyone a favor and leave nothing unstated. Volunteer your motivation, if you must: “Let me just say how much I appreciate the opportunity to interview for this position because I’m very interested in your corporate immigration practice,” or what have you. Do not let the interviewer assume that you are simply looking for any job.

Side note on interviewing with regional or national law firms: law students often wonder, “how do I evaluate full-service law firms when they all look so similar? The honest truth is that I’m just trying to land a gig with ANY law firm.” It’s worth acknowledging the validity of this assessment, particularly with respect to full-service nations firms. After all, much of their business model and compensation structure are meant to look like those of “peer” firms. It’s also true that few law students or junior lawyers know enough inside baseball to credibly weigh law firm reputations. Besides, the hyper-competitive nature of law firm recruiting usually means the firms enjoy much more optionality than candidates. All that said, candidates CAN and SHOULD develop a baseline understanding of how an employer wishes to be viewed by the world. Study the website and understand recent cases or developments in which an employer has been involved.

Why should I trust you to do the job?

This may sound tautological, but it is worth stating in black and white: a hiring manager’s most important decision is who to hire. That decision will forever bear on a hiring manager’s reputation and credibility because the hiring manager’s performance will be measured by the performance of their team. So there isn’t a snowball’s chance in hell that a hiring manager will go out on a limb for you, as a candidate, if you cannot convince the hiring manager that you have exercised sound judgment and execution skills in the past, and are capable of doing so in the future. The interview is your opportunity to sell a hiring manager on that notion. And since interviews are timebounded, you’ll want to practice ahead of time.

Some candidates may approach an interview with more of an ad hoc approach, where their primary task is to answer questions without flubbing. You should certainly seek to anwer an interviewer’s questions with poise and clarity. But it would be a mistake to stop there. Hone your pitch ahead of time by answering for yourself, “why should I be trusted to do this job?”

Why should I want to hire you?

Lawyers, especially those early on in their career, spend an outsized number of waking hours working, usually with colleagues. You’ll pull all-nighters, share meals, imbibe, laugh, cry, gossip, sometimes even share lodging. (True, funny story: I once had to share a small Springfield Suites-room with a partner who failed to book a separate room. That night, I learned that he snores and wears flannel boxers.)

Given the literal and figurative close quarters that await you, you had better believe that an interviewer will be assessing whether they can work shoulder-to-shoulder with you for 12 hours straight. At the end of the day, an employer has to like you to hire you.

Resume-writing tips

Over the last four-and-a-half years at Affirm, I’ve reviewed thousands of resumes from job candidates, ranging from entry-level attorneys to seasoned 25-year career veterans, applying to the dozens of job openings my team has filled over the years. Nobody, then, should be shocked to learn that I spend, on average, 30 seconds reviewing a resume the first time it hits the proverbial desk. Of course, I’ll spend much more time with a resume if I’ve decided to follow-up with a candidate, but the initial review process is shockingly swift. And while my recruiting colleagues might spend a bit more time with a resume during an initial review, I doubt it’s materially more time.  

Given these constraints, the best resumes are those that allow me to scan quickly and efficiently. If I cannot consume your grock your candidacy for a role in roughly 30 seconds, your resume gets set aside. It’s worth, then, understanding what makes a better resume.  

Here’s a quick & dirty resume-writing guide I wrote for law students and young lawyers. I’ve organized my thoughts into two main buckets: (1) resume content, and (2) resume format.


Resume Content: You can overcome poor formatting with strong content, but not the other way around. Here is where you should spend 80% of your time when writing a resume.

– Go slow. Start with pen and paper and list your schools and employers in reverse chronological order. List corresponding dates of attendance/employment next to each school/employer. List your degrees under each school, and your positions under each employer. You may have multiple degrees with each school, or multiple positions with a single employer, as the case may be. Under each position, write all of the (1) recurring responsibilities, and (2) notable projects you executed in a given position. The reason I like to start with pen and paper is because it helps jog my memory in a way a keyboard cannot. Once you have everything on a page, then you can proceed to refine in a word processor.

– Describe prior responsibilities with punchy action words. For prior positions, I start each sentence/bullet with a past-tense verb. For current positions, use the present tense. For example: “Drafted/draft legal memoranda assessing claims and defenses of XYZ client” and NOT “Responsible for performing legal research…”

– Specify and Quantify. Specify your accomplishments by identifying specific results or milestones. How did your project or initiative advance your employer’s objectives? Did your successful motion to dismiss defeat a claim for breach of contract? Or, did it defeat a $100mm claim for breach of contract?

– Edit for specific audience. It’s fine to have one master resume, but, before you send a resume to a prospective employer, you should tailor it based on the audience. For instance, if you know you share a particular interest with someone who’ll be reading your resume, highlight that.

– Maintain integrity. Don’t embellish, and certainly never lie. If you were part of a team, say so. Don’t claim credit for yourself when it should be shared. Some of the worst resume-offenses I’ve ever seen involved gross embellishment of a person’s responsibilities on an assignment or project. Such matters are easy to spot and verify through back-channel references. (And, yes, employers often do back-channel references on a candidate.)


Format: Remember, most first-level resume reviewers will read your resume very quickly because they’re battling through a stack of other candidates. The format of your resume must help a reader scan its content quickly and efficiently.

– Font: Use a clean sans serif typeface like Arial in a font size of at least 11. (Truthfully, I can make do with font size 10, but that is becoming less and less true as eyeglass prescription changes.) The point is, this is not the time to get cute with fonts. While you’re at it, just forget that Comic Sans was ever a thing…

– Sections: Generally speaking, include (1) education, (2) professional experience, (3) honors & awards, and (4) activities & interests. (Quick note on “activities & interests,” omit this section at your peril! Here’s where you convey more of your personality outside of academics or work. An employer needs to believe that you’re both qualified and they’ll want to work with you.)

Feel free to include additional sections if you believe warranted by the prospective audience or position, or if you think there is something categorically unique about you. For example, if you are an accomplished speaker or writer, that may merit its own section.

– Sequencing: If you are a new or recent grad (i.e., graduated w/in the last three years), stat with the education section and follow it with your experience section. If you’ve been out of school for three years or longer, consider leading with your experience, particularly as it becomes more relevant to a prospective job opportunity. 

– Length: If you’re a new or recent grad, there’s little reason that your resume should be longer than a page.

Personal Lessons About Team-Building

Over four years ago, I was tasked with the enviable project of building from ground zero an in-house legal and compliance team at Affirm. Given my dearth of prior experience, I had no business managing such a project, and each hiring decision was fraught with self-doubt: could I successfully harness this person’s talents and experience without outing myself as a fraud?

Four years and dozens hires later, I’ve grown more confident in my team-building role though I find it no less challenging — and certainly no less critical — today than it was on day one. With typical year-end reflection, I thought now would be good time to reflect on and share three lessons learned.

Get over yourself: Your new team members in many ways will, and should, be more talented and forward-thinking than you. After all, this is precisely why you’re hiring them. One person alone cannot possibly have perfect knowledge and judgment, and it is unreasonable (and potentially stupid) to think oneself master arbiter of all questions. Healthy dialogue with a talented team will always yield better results.

Share information early and often: Think about the onboarding process and how you might best set up your new teammates for success. Transfer your knowledge about the business to each new hire in digestible, actionable bites. Who will be their primary points-of-contact for the lines of business they’ll support? What are those personalities like? What are the organization’s communication channels? The more efficient this knowledge transference, the better your new teammates will be able to bring their unique expertise to bear.

Think ahead 2-3 years: When we started building the legal and compliance team, it was very tempting to hire for more immediate and discrete needs. Luckily, several friends and colleagues advised against this temptation and urged me to think about higher potential candidates that could grow a job function instead of just “keep up” with a job function. This is admittedly challenging particularly when staring at a mountain of immediate work. Still, it is well worth taking the step back and thinking about what the needs might look like 2-3 years out.

Accept change: The team you build today will not be the team you keep. I’ve been struggling with this a lot lately because of some recent “regrettable attrition.” Change is a fact of life, and it can be quite healthy by forcing a hiring manager to constantly consider retention. But even when your team inevitably loses a high performer, it could be because of the opportunity you, the hiring manager, afforded them. That has to be worth something. Besides, people can always decide to return.

Building the legan and compliance team at Affirm remains the most rewarding and challenging experience of my career, and I am thankful for the opportunity to have “learned on the job.” In sum, I suppose the biggest lesson I’ve learned is that it’s okay to not have all the answers. But it is important to ask the right questions even at the risk of revealing ignorance. After all, teamwork makes the dream work.