We are the stories we tell ourselves. But what happens if one day that story changes unexpectedly? It causes trauma, but also change. Realising we have the power to shape our own narrative and not be defined by external notions of success is empowering.
This is the story of Olatunji “Tunji” Williams.
Tunji Williams’ career is a rich tapestry. He’s run political campaigns, been a Big Law M&A lawyer, founded a legaltech start-up, led growth at Litera, and today is co-founder of ShareThing, a social entrepreneur at the forefront of the fantastic buy nothing movement.
Tunji’s path is a heartfelt hymn to the fact careers are journeys rather than destinations. And like all journeys, there’s ups and downs, twists and turns, the unexpected and the serendipitous. We also touch upon the important interplay of cultural identity, imposter syndrome and how these push and pull on our ideas of success, access to experience and careers.
We applaud Tunji’s generous authenticity, and hope this interview inspires others!
Tunji, how did your career begin?
The funny thing is that you don’t just wake up one day and say “today, my career starts”.
I think when you look back, you actually realize, ‘Oh… my career started someplace else”, and it’s not when or where you would think.
So looking from the outside in, ostensibly my career begins at Hogan Lovells after law school in October, 2014.
That’s when I began my M&A practice.
I thought I wanted to learn how to become a world-class counselor to business titans and all that. That’s when I thought my career started.
But when I started thinking about this more recently, I realized that my career actually began when I was 19 years old – when I had the opportunity to manage my first political campaign.
How did you land that opportunity at such a young age?
I landed the opportunity by being naive and audacious!
I was a member of the young Democrats club in the town where I grew up and regularly attended the weekly meetings on Thursdays after school.
I would always look for opportunities to latch onto people, learn, and then use the learning to do something new. These were people that impressed me, that rose above the ordinary.
And one of the earlier meetings I attended, there was this guy there named, Calvin Ball. At the time he was the councilman for the 2nd district in Howard County, Maryland where I’m from.
I saw him speak, and I thought to myself, “wow, this is somebody I’d love to be like”.
So I asked him if I could intern for him over the summer. And he said, yes!
That summer interning for Calvin was my first career defining role, and I began to realize what actually gave me joy. It wasn’t money – I didn’t get any money at all doing that job despite working four days a week.
At the time I didn’t realise it, but I was learning what I love.
So that was the actual starting point for my career. It makes for an interesting dichotomy between the outside-in view, and what I’ve come to realize much later in life.
When you were 19 interning for Calvin Ball, what was it specifically that you figured in terms of broader and longer term career ambitions?
I wanted to be known for something. I didn’t want to disappear in history. I think I was, even at that age, driven by that. I saw that politicians seem to get a platform and leave their imprint on the world. So I thought I wanted to be a politician.
What I drew joy from the most was the constituent services part of politics.
I enjoyed writing to people, checking in on people who were struggling to pay their electricity bills, hearing people’s stories and realizing how similar I was to everybody around me and that I wasn’t quite alone and neither were they.
At the same time, I knew that others viewed this sort of thing as drudgery; the sort of thing you have to do at the start before you get to wear the suit and tie and be on TV.
What surprised me was how much joy I got from the constituent services work. It wasn’t the drudgery you’d expect, at least not for me.
Politics and law have a natural and easy overlap, and a lot of politicians have a legal background. Did having a start in politics inform a decision to go into law?
They were informed by one another. Absolutely. I was always going to go into law. That was my destiny. It was written.
I come from a family of barristers and attorneys going back several generations. It’s in the family, in the blood.
My grandmother was a barrister who trained in England and moved back to Lagos, Nigeria where she was chief magistrate.
Her father was an attorney. My dad actually took a different path and became a physician. But I always felt I was, I was headed that way – to law.
Stepping forward into your legal career in 2014, did anything change as you progressed down the lawyer track?
What changed is that I got scared shitless. Six months in, I was just scared. I was really scared because I looked around and I saw the level of perceived excellence, determination and grind. It was all around.
And I wasn’t sure I could maintain the mask long enough to get things I thought I wanted.
That scared me a lot.
It led me to start asking questions about my existence and my role in the organization and my curated life. I just… I just fell into this, this kind of malaise, because the more I thought about the business, the less I understood it.
How does the money actually move? Why are we getting paid this much to do this? How do the people on the other side of this know that I know enough to produce value? Who is quality checking this? Why am I the best person to do this? What do I do after I know how to do this?
The more questions I asked, the less I understood the path ahead of me. And that made me concerned.
I’m the kind of person that once I ask one question it leads to a second question, and on and on. I can’t stop.
And there wasn’t much room for that type of curiosity in the strict, kind of confined way we choose to practice law.
That’s what led me to look at other things.
And first, before I got brave, I experimented with other things. Other things meant trying to buck the traditional trend, and see if I could skip ahead and start bringing in clients and prove how valuable and smart I felt I needed to be.
For me this was a way to stop being scared.
That was going to be my story. In my head I wanted to be seen as the whiz kid rainmaker. So, I was looking for every opportunity to impress my boss at the time, David Gibbons, who is now global head of corporate at Hogan Lovells, and was a very senior partner even back then.
David also gave me my start – he was the guy responsible for interviewing me and giving me my job (and I’ll always be grateful to my fairy godmother, Randi Lewis, who set up the fateful meeting).
So one day I stir up the courage to walk down to see David, two doors down from my own office, and say “Hey David, there’s this company called FiscalNote, I want to tell you about…”.
FiscalNote was, and is, run by this guy named Tim Hwang, who I knew from Maryland political circles. At the time there was a glowing article about him in Bethesda Magazine asking if he’s the next Bill Gates, so I get in contact with him.
My suggestion to my boss at Hogan Lovells, David, was that we should represent this up and coming company pro bono. This was going to be big.
And David being, charitable and encouraging said, “go for it!”.
So I brought Tim in, I offered to take Tim to an Orioles baseball game, mimicking the partners I’d seen on TV and all the things I thought partners did. Tim, to his credit, politely declined the dog and pony show.
I, instead, invited him into the office and I walked him around, like a true rainmaker. I stopped by all the powerful partners’ offices on my floor and said, “this is Tim Hwang. He just inked a deal with JP Morgan, and there’s this article about him in the Bethesda Magazine, and his company is going to be huge etc”.
And they’re all just like, “great Tunji”.
What they didn’t tell me immediately – because they didn’t want to discourage me, is that, “you know, Tim can’t afford us yet”.
When I figured that out, it blew my mind. I couldn’t stop thinking: “He can’t afford us?”.
When you start to think about that deeply, it’s actually really backwards.
How can an entrepreneur who has proven fundamental value in the market and demonstrated the growth potential of a product, not afford world-class legal services?
There’s a fundamental and costly misalignment when an industry’s pricing model and standard mode of delivery are so rigid, as to prevent the top law firms from considering future growth potential in evaluating the suitability of accepting young companies as firm clients.
So that led me to think, “man, I gotta go face-to-face with this thing for myself. I can’t have anybody between me and real learning.”
I started talking more and more with Tim and told him, “look, man, I don’t know if this is the right time for us to represent you as an organization, but I want to be super-close in any way I can help. Just let me know”.
From then on, I couldn’t stop thinking about FiscalNote for months. I was telling everybody I knew about FiscalNote and introducing people to Tim, to the point where I thought “I’d be pretty good at FiscalNote, on the inside. Let me see if I can get a job there.”
And did you join FiscalNote?
Yeah. I went to go join FiscalNote, after being at Hogan Lovells for only seven months.
I was scared out of my comfort zone into this world of enterprise technology, which I knew nothing about at the time.
And I’d also gone from earning $160,000 per year to $39,000 a year, and in addition, having to travel an hour to work an hour back on the train every single day.
I started at the bottom. I was a business development representative and I was selling FiscalNote’s technology to law firms, including Am Law 100 law firms.
Just to pause there, for readers unfamiliar with FiscalNote, do you mind elaborating on the product and its use cases?
Sure. FiscalNote crunches data and produces predictive algorithms that analyse legislative and regulatory data. That analysis is used to score the probability that a piece of legislation or regulation will pass at different stages of the legislative or regulatory rulemaking process. In some cases we could do this with around 97.6% accuracy.
FiscalNote could drill down to the level of individual legislators and analyse the probability they would vote for, or against, the legislation in question. This would be helpful to any individual or organisation seeking to lobby and influence policy outcomes, i.e. you have a better sense of where to focus your political and financial resources.
They were also using tools like sentiment analysis during the rulemaking process to discern advance signals as to which way the regulators were leaning at a given point in the process, which could provide an edge to businesses or other policy makers and interested individuals.
I thought that was really cool. And for me, what it stood for was an opportunity to really democratize, and make better use, of public information, in order to help people and businesses make better decisions.
My personal thesis is that when everybody gets access to the same information, we see the best and the brightest rise to the top. We need to live in a world where that’s possible. Asymmetry of information is a powerful tool used to consolidate and concentrate power for the few. Open access to information is the antidote for the rest of us.
That’s a really interesting take. The printing press and the internet have successively reduced the cost of information sharing and thereby democratized access. The rise of MOOCs is amazing too – you can teach yourself a course taught by a leading university, often for free so long as you have a basic smart device and internet connection.
Do you see any caveats to making information more easily and widely available, especially where it can be used to inform decision-making?
Definitely. Information can set you free but can also entrap you.
Not all information is good information, let alone correct information. There’s also a need for wisdom. I think wisdom comes in different forms, but at its essence, it really is about having the understanding necessary to truly discern signal from noise.
And that can be gleaned via an algorithm, or the way it’s been done throughout human history – passing knowledge and wisdom down from one generation down to the next, through our families, tribes and broader communities.
Moving to Fiscal Note, that was a big move early on in your legal career. How did things pan out?
I’m going to be really honest with you throughout this whole thing, because I think that there might be wisdom in my story that I don’t even know about yet, that may help other people.
So I’m not going to sugar-coat it.
In general you need to be honest with yourself to understand yourself. The more you deny yourself, the further away you get from understanding and the further you get away from understanding, the further you get away from truth, and the further you get away from truth… well, it doesn’t end well!
So for me, when I was at FiscalNote, I was free in a way, because the future was unclear.
And I was looking for that at some level.
But my pride and my ego made me feel that I deserved something more. I had this narrative in my head that went something like this:
“I’m so smart. I had made it into Big Law. I made this decision to leave law. I’m so great. And I have a law degree from a great school. I shouldn’t be a sales rep. Are they kidding? How long am I going to be in this role? I’m ready to be a VP of something. I’m ready to be the big boss. I should be earning more than $39,000. I know the value of my labor and training etc.”
Those thoughts, those tracks, those scripts were holding me back from doing all the learning that I should have been doing.
So the learning I could have done in three months took me six months at FiscalNote because I had to move through those scripts.
I want to just step back and say that this is related to the same angst, that same script, I had while I was at Hogan Lovells. That script was telling me:
“$160,000 a year. You can’t be worth that much. They’re going to find out about you, man. Just stay inside the lines, shut up or do something different, so they don’t focus on the fact that you truly shouldn’t be earning that much money.”
It was a script about self-worth and proving my value.
Not only to others but to myself. It got in the way of me learning what I could have been learning while I was at FiscalNote.
I was focused on trying to understand my worth and my value, which is not a worthless pursuit. The irony is that you actually build real value in your life by allowing yourself to fully experience all that is right in front of you. That requires you to be genuinely present and mindful, and in so being, open yourself up to the hidden gems of wisdom, invisible to the undiscerning and distracted eye.
Whether or not you like the taste of that fruit, that experience, it nourishes your body. You learn more about what you like, what you don’t like, what you’re good at, and what you’re not. You need to learn this about yourself to move forward.
But in a nutshell, while I was at FiscalNote, I just got proud, man. That’s the honest truth.
And so I decided to go back to law. I wanted my fancy suits back. I wanted to do that type of work again. I wanted to be able to pay my loans that I’d been deferring – $350,000 worth, which are still pretty high because of the choices I’ve made.
So, I went back.
I went crawling back to David who was my guardian angel in many ways. I said “I think I learned what I had to learn”. I felt I’d screwed up, but really I hadn’t. But that’s what it felt like. I did, however, feel the business experience would make me more valuable as a lawyer.
But after I went back, I found the same thing again, the same script playing in my head. This time I lasted 11 months. I almost got there – to acceptance (or resignation, depending upon how you look at it), then I left again.
I‘ve quit my job six times since I graduated from college, I’ve been on a journey.
What led you to that decision point?
I hadn’t developed frameworks for life yet. I was still freestyling. And that freestyle-heavy life is like playing jazz.
Your soul kind of leads you to where you’re supposed to be. So it’s okay. But sometimes, you make a mess, and at other people’s expense. Even if the music you produce is beautiful, if you’re playing too loud and not in consideration of those around you, it’s hard for any tone to really groove with you, you know what I mean?
I didn’t have a framework, and I left because I was feeling uncomfortable.
And then, something else happened.
Back in 2015, there was an incident that happened in Baltimore, where I was living and working at the time.
A guy by the name of Freddie Gray was killed by the police in West Baltimore. And it caused massive unrest throughout the city. You know, people hurt and righteously enraged by what had happened to their neighbor, were seeking and delivering justice.
It was mesmerizing chaos in the city, and the whole time I felt more with the People, than I did with the people in my office. Not because the people in my office were wrong or bad. They weren’t. In fact,they held opinions just like mine about what was going on. They understood, they felt, they empathized, but they weren’t me. They weren’t my people.
Every day when I drove home from work, I felt like I was in the wrong place. I was missing. I was missing my life somewhere else. I was in somebody else’s body.
And it got to a point where honestly, I couldn’t leave my apartment for two weeks. I was in a deep depression. Really depressed for two weeks, my last two weeks at Hogan Lovells in December, late 2015.
So this is post-Freddie Gray, which happened a few months prior to that. But the city was still under the cloud of that tragedy. And I was just at this point where I was like, “I don’t know what’s next for me, but, I know this isn’t my life. And I don’t know what is my life. I just don’t know what to do.”
I was lost and very scared.
And so I called in sick, day after day, for two weeks straight. And I was on the floor in my fancy apartment, wearing the same clothes.
This was obviously a very rough and disorienting period for you.
Yeah, it was tough. As you can tell, it’s upsetting for me to speak about this period, but… I’m pleased that I’m on the other side of it, but it was… it was tough. It was worrisome. And I just knew that I had to be doing something else.
And this is where a friend of mine by the name of Reggie Fugett helps me out.
A lot of stuff happens like this in my life, where it’s just like, why me? Why now? You know, it’s not me. There’s something bigger than me at play here.
Reggie reaches out to me and he’s like, “Hey man, just wanted to check in and see what you’re up to?”.
And Reggie surprises me, he says, I’m thinking about running for city council in West Baltimore.”
So, we talked about it.
For context, we had been introduced four years earlier by a mutual friend while I was at college in New York. They’d said “you need to meet this guy, he’s the nephew of the first black man to ever build a billion dollar company in America, Reginald Lewis, and he’s from Baltimore, where you grew up. You should get to know one another.”
That’s how we initially connected and we had some conversations, but we never touched base again.
It’s kind of strange that we meet later again at this point in my life, and he’s like, “let’s meet up to discuss this campaign I’m about to launch.”
So we meet, have spaghetti and over dinner, and I decide to leave my job and run his campaign for a thousand dollars a month. Cheap date, I know.
Very soon after we went out in West Baltimore and we built the campaign from scratch. Just the two of us, out of Reggie’s childhood home. And from that, we quickly built the campaign to 150 plus volunteers.
We raised the most money that had ever been raised for a city council campaign in that district. Our campaign was also unusual for the fact that in a city with as rich and structured a political tradition as Baltimore, folks rarely enter the fold without asking permission.
You don’t just jump in (as we did), and try to win. Fortunately, we didn’t know any better.
How did the campaign go?
We came in second out of a field of seven candidates, and a very close second to the dedicated, long-time community organizer, Kris Burnett, who ultimately won the race.
The close loss notwithstanding, I felt truly at home during that process. I was with my people, even if I didn’t really know that part of Baltimore well yet. I learned a whole lot in that four months. I was back where I belonged, and that was grounding for me in the best way.
This sounds like an important and timely turning point for you?
It was. But I don’t want to mix issues here. I want to be really clear, maybe at risk of offending people. But my intent is good when I say that I wanted to be with my people.
By that I mean Black people. And I say that, not because I don’t have love for all people. I have immense love for all people. I do. And you can’t really love yourself if you don’t have love for all.
When I talk about black people, it’s worth me explaining how I grew up.
I’m from a country called Nigeria, a former British colony.
Very early, we’re taught how to hate ourselves. And love everything that was British and white, and see that as good and the path to success and esteem. Everything else that you are is to be hidden at all costs and that kind of suppression leads, I think, to collective neurosis.
It’s multi-generational and it infects the mind and the soul.
The difficult part about it is that ostensibly you may be doing well, really well perhaps; you’re progressing through society, as one is expected to do. And you might even be outperforming those that look like you.
But inside there’s a fundamental dissonance with respect to your identity.
Between what you are and what you think you need to be, or what others think you should be or stand for.
All humans experience that on some level.
But when you mix that with this complicated dynamic around racial and ethnic identity, it can become combustible, if not addressed. Left unattended to, the resulting trauma begins to manifest itself in one’s life in destructive ways.
I wanted to offer that in technicolor for the readers, for clarity’s sake..
My whole life I’ve existed in white spaces, where I was pretty much the only black person… forced to be a symbol for all that I represented to the people in control of those spaces. It’s tough. It’s tough on the young mind, because if you’re somebody like me, who likes people, and wants to please people you want to be for them, what they think you are.
It’s confusing and it’s a lot of noise and not much signal. So I was feeling mad at a spiritual level. When I left Hogan Lovells the second time. I needed to go wherever I could go unnoticed, somewhere I don’t need to be a symbol, so I could be closer to who I am.
That dissonance sounds very disorienting, and stress-inducing.
Definitely. This struggle is pervasive to anyone who doesn’t fit the standard profile of what society expects for this or that.
This concept is nuanced and robust and there’s lots more to it, but it’s broadly about looking to projections of other people’s desires as a guide for what you want.
In Girard’s terms, that’s mimetic desire: a desire that’s derivative of somebody else’s desires and that you make your own. And it creates a duplicity of character that can become troubling to you over time.
He also talks about this adjacent concept of coming face to face with your idols. He explores what happens when you achieve the same level of knowledge and access to information as your ideals and what happens as a result?
He warns that you’ll want to fight them, literally or figuratively. It will create conflict in you. And that’s not what you really want; what you really want is understanding and self-actualization.
It’s part of growing up, I think, to try and get comfortable in your own skin and say, ‘this is how I am going to define my own success and what that means to me, and how I get there from where I am right now’… and not be too influenced by other people’s notions of what that is. There’s a lot of social, racial, class and familial pressures to do certain things in a certain way and in a certain order, or be limited in some way as to who gets to achieve what in life.
Speaking of which, you come from a long line of lawyers, and you mention it was ‘written’ that you’d become a lawyer.
Did that weigh heavily on you when you decided to leave the law for good?
Absolutely. There is this idea of identity. The stories we tell ourselves about who we really are.
If you read a certain bedtime story to yourself about yourself every night, and then one night when you’re 27, you decide to stop reading that story. What happens? It causes trauma.
You feel a sense of loss. You feel a sense of betrayal, to your origin, to your narrative. And it’s hard to get over that..
So yeah, that’s tough. It causes trauma, but I think once you have that realization it’s not so much about freeing yourself from a particular identity, as much as it is about recognizing that identities are created. Once you get there, to that epiphany, and unlock it can be incredibly liberating.
That’s a great way of putting it, the idea that we are the stories we tell ourselves. This realization must have been very impactful. How did it influence what you came next?
Well, those campaigns are a funny thing, because they only last a little bit.
And then you go back to real life and.. my real life was $0 in the bank account, $350,000 worth of debt still with interest accruing at various high rates and… no immediate job prospects.
There were folks that approached me, who liked the work that we did with the campaign and wanted me to maybe think about getting more involved in helping politically on other stuff.
But it wasn’t about getting ahead in politics for me, it was more that this experience had really built me up again as a person. That was bigger than an election to me. No next political gig could compare.
So I just reached out to this firm that I interned at when I was in law school called Miles & Stockbridge, and I pretty much just begged for a job.
I really liked the culture of the firm, which I do and did.
Luckily for me they took me on (thanks, again, to my Randi Lewis – my fairy godmother), and I was there for a year and a half. I have all the love in the world for that firm, and the people there. The lawyer, for my first company, and my current company – Venroy July, is an equity partner there. I’ll always be faithful to them. They’re a great team.
So you get back into being a lawyer at Miles & Stockbridge and reach a happier cadence, and then at some point you decide to start dealWIP, a deal flow management platform?
Right. I realize now that dealWIP was about something different than what I thought it was about at the time.
I’ll tell you what I thought it was about.
First, I was experiencing a lot of anxiety at work, like we all do. There was a delta between what people were expecting from me, and what I felt I could consistently deliver, irrespective of whether and what I actually did deliver, which 75% of the time was what they wanted.
Second, it was really tricky and stressful trying to keep track of everything coming at me each day, across so many different contexts, all seemingly at a million miles per hour.
Third, as wonderful as the people were at Miles and Stockbridge, if you work in law as a young black guy, there aren’t a lot of people that you can relate to, or people that feel that they can relate to you. People want you to win generally. I do impute that motive to most people, they want you to win; they recognise we don’t have enough black people succeeding, and we want this to do well, but they don’t know how to approach us. There’s worry about the risk of coming across as glib or condescending.
And I empathized with the seemingly powerful white people around me. They wanted to protect and push me forward, but didn’t know how, right? Of course, some people in life don’t want you around, let’s not gloss over that. So, bottom line, I felt like I was blowing in the wind sitting there, waiting for someone to save me.
I didn’t feel that I had anyone showing me the real blueprint for success – other than Venroy, who tried desperately (but I was too stubborn, and he was so busy trying to keep himself in the race – a 24/7/365 job for a black person trying to rise through the ranks in corporate law). I felt like I was getting the brochure all the time, from all angles. And you can’t really learn how to do something well with that, you can find the brochure bullshit on the internet.
What I needed was someone that was like, “you want a client? Here’s what you really need to do”.
So I started thinking, “how can I get access to that?”.
And how did you get to that knowledge and experience?
So, we moved to the States from the UK when I was 8. A lot of Nigerians have ties to the UK and I lived there with my Mum, Dad and brother until 1997.
That meant that as a family, we didn’t have a ton of lawyer contacts in the States that I could call up and say “hey, can I work at your firm? Tell me the partner to work for. Can you mentor me etc?”.
I just figured it out on my own. I was my own game tape.
What’s a game tape?
A game tape is when you record a performance – sports, music, anything really – and play it back to understand what worked well, or not so well, so you can optimize the former and minimize/mitigate the latter to improve.
What I wanted was to build my own game tape collection. This is what I did to get good at politics, and how I’m learning to be better in business.
It’s by analysing people I think are excellent at this or that, and then deconstructing why that is, and then initially mimicking those abilities and eventually making them my own. Finally adding my own flair. It’s part science, part art.
Got it. And how did you build up your legal game tape? And how does this relate to dealWIP?
OK. So I couldn’t figure out how to get game tape for the lawyers I saw really doing well.
For instance, just seeing their documents wasn’t enough. There’s no annotation, commentary or context. The stuff you really need to know to understand how and why they did what they did isn’t there. You also don’t have any easy way to record their calls or negotiations and figure out how they influence, persuade, manage clients or to dissect their bedside manner. How do you talk to the CEO in a way that inspires trust and quick confidence?
It’s all these little things, that in aggregate, make the difference between an OK lawyer and a great lawyer.
Sure you get some exposure to this each time you work with someone, but you might not always get to work with everyone, nor with the best people enough of the time.
You also need breadth and depth of these experiences. That requires seeing and understanding the full spectrum of all performers, to some extent. It’s hard to assess who is better at this or that without having some baseline against which to compare.
I started thinking the reason I can’t get access to all of that and further my learning and development, is that we don’t have integrated work systems.
I can’t tap into a matter and see every communication related to that matter, every phone call, email, every iteration of a negotiated document, everything.
And I wished I had that so that when I’m not getting work, and have some downtime, I can study top performers and make myself more objectively valuable to the organization.
The idea was to create that environment for that purpose, both to consolidate deal data into one single source of truth in general, but crucially, as a means for junior lawyers to level-up and gain access to those game tapes, to better themselves and learn from the best.
That makes sense. Having all the deal data, but as you say, crucially the context about why something was done a certain way, which leads into the what and how of the matter. If you only see the finished product, absent of context, you can’t always tell what is good, bad or mediocre legal work product. Some of the clause library tools we’ve seen fail on this, providing syntactically similar clause groupings but lacking any real context as to whether the clauses are buyer or seller friendly or highly context specific. Without that, you can’t learn effectively. You can’t know good from bad, nor importantly why each is which.
That’s right. It’s made worse by the fact that in law school, we’re taught to be direct-match learners, instead of first principle thinkers. You’re given a fact pattern, asked to find a legal precedent that is as close as possible to a direct match, and apply the precedent to solve a legal problem.
Rarely do you get into first principles in the true sense. You don’t enquire in the sense of asking “What’s going on here. What are the forces at play? What are the mixed incentive frameworks? Let’s analyze this at a really foundational level.”
I think the people that outperform the crowd, are first principles thinkers and not direct-match thinkers. It’s the difference between looking directly at the sun, and at starting the shadowy reflections in Plato’s allegory of the cave. I like to come face-to-face with the sun. It’s where I’m most comfortable. I prefer life outside the cave.
Having worked in politics and law, how did you find that transition to being an entrepreneur?
DealWIP was actually my second business. I started my first business, Stratosphere Records when I was 12 years old. My buddy and I, Powell Perng, had that company going through until 2003. That’s not on my LinkedIn. That’s too embarrassing!
That company was so much fun. We made a lot of music together, designed t-shirts, built a make-shift recording studio in Powell’s parents’ basement, and charged classmates to record with us. We even incorporated a company in Delaware. We did everything completely wrong, but we learnt a ton, and we had a blast. We were practicing how to create and build things from nothing.
With dealWIP, I left Miles & Stockbridge and raised a bit of money to build our prototype. I thought building software was going to be way cheaper and faster to build than it turned out to be. I’ve never made that faulty assumption again. I managed to raise additional funds, I think based on the confidence I conveyed to early investors and my vision about the future of the product and the industry.
The little success that we had, was as a result of the way we were thinking. I think our generous early investors thought, “this will lead to something good, even if it’s not this version of the company”.
Thinking back to what you said before about game tapes. Did learning from mentors to understand why and how they were successful at building that trust and quick confidence help you have those early conversations to win investment and build a team?
The answer is no, unfortunately. I never actually got that inside track training. Not because anybody was trying to deprive me of it, but more because the general dynamics at play when lawyering don’t foster too many of those opportunities to really understand why and how top performers are great.
But what I did get was an understanding of what convinces highly analytical people of your point: how to convince people, how to make a case, a strong argument and support it with substantive analysis.
That was what I learned; frameworks for reasoning.
Those were fundamental in helping me – as a first-time entrepreneur – to convince people quickly, and to the tune of hundreds of thousands of dollars.
Do you have any tips in that regard?
So number one, is to understand what’s important to the other person. Once you understand the other person’s operating system, you can make better assumptions, let’s say. You never make perfect assumptions because we’re human – we’re mired in our own bias.
But you can make better assumptions and you can ask the right questions. So, start there.
Number two, understand their mental models, their favorite mental models. How do they approach the world and think about the world? What are the biases that are most adjacent to their everyday logical thinking?
And from there, I can understand how they perceive facts, how they decide what’s most important, not just what they say is most important to them. People are often unreliable narrators in describing their own deepest motivations and triggers. And, if I see that there’s a mismatch in what they say is most important to them, and how they got to that conclusion, then sometimes there’s an arbitrage opportunity in a relationship, where you can help somebody get better results for themselves than they could’ve gotten independent of your input.
That’s how you demonstrate value. It can feel like a magic trick to the uninitiated. But, it’s really just about focused and intentional listening, and the bold, empathetic and genuine pursuit of understanding in each human interaction. I learned that framework from watching really good lawyers advise.
You’re right. The best sales people I’ve worked with, or had sell to me, have understood what you’ve just described. Sometimes 4 or 5 targeted questions into a sales conversation that person is able to laser in on a need, and that need is the nail they hang their pitch on and win over the prospect. The best make that invisible, natural and easy. It’s quite an art.
He says that there’s a distinction between technique in social interactions, and behavior.
People can tell when you’re using a technique. It feels inauthentic. But when you practice a behavior that you’re using invariably in every single situation, it feels and looks consistent and true to who you are.
If you start asking lots of incisive questions out of nowhere, and it’s out of character, people will naturally be like, ‘hang on, Tunji doesn’t normally ask this many questions? What is he trying to get out of me? What’s his angle?”
Now if you adapt your behaviour and make that curiosity a genuine and natural part of who you are, and your everyday rhythm, not only does having those conversations become easier, but you will also be more successful when you have them.
It will be easier for you to understand people and their drivers better without it being weird.
That’s very true. As a buyer of legaltech, and running this site, we get sold a lot of products. It’s noticeable when someone has learnt a technique but not yet mastered the performance if that makes sense? Using people’s names – as suggested in Dale Carnegie’s How to Win Friends and Influence People – is a good example. It’s a powerful social skill when used effectively, but selectively. Too often people misunderstand that tip and overuse names to the point it sounds totally unnatural and, to be frank just plain weird.
Absolutely. Technique versus behavior is about integration. And like any good integration, it needs to be seamless, natural and ideally invisible.
Technique is something you do. That’s something separate from yourself. Behavior is who you are, right?
What you think becomes what you say, what you say becomes what you do. And when what you do becomes who you are. It becomes behaviour.
It’s easy to say, but tough to understand.
Technology is like that. It’s best when it’s invisible, when it flies by you and you don’t even notice it. On that point, returning to tech for a moment, you built a tech start-up from the ground up and ran it for several years. What happened next and why?
Over the course of those two years or so, we raised nearly a million dollars to build up a team and a product.
We’d seen reasonable growth. But as you know, it takes 18 months minimum to land the big law firm sale. Even at Litera – which we’ll get to later – that has such an entrenched sales channel, it’s still a 12 month process.
For start-ups as small as we were, you aren’t necessarily well positioned to do well in that contest, unless your offering is so differentiated that the customer, or the market in general, is willing to compress the sales cycle.
It takes a little bit of naïveté to believe that by will and power of personality, you’ll be able to alter that dynamic. And naïveté is exactly what we had.
We were encouraged by having gotten into the Lexis Nexis accelerator and MDR Lab. We felt that maybe there was something fundamentally valuable about the way we were doing this, or perhaps our brand or message that resonated with people.
That encouraged us to keep on going. Even if the product wasn’t coming together as quickly as we would’ve liked, a lot happened over those two years.
We pivoted slightly with the product direction, narrowed our scope in response to the feedback we got spending three months at MDR Lab in London. That was when our hardcore development happened, helped along by being there with the people who would use it everyday, and getting out of our own assumptions and our definition of the identity of the product and moving instead into a user-led understanding of what they needed and wanted from us.
That was beautiful and edifying. Humbling, too.
But at the end of the day, we didn’t have enough revenue or enough customers to convince the market that we were ready for a seed round in the two to three million dollar range.
I could not find anybody to invest at that level in time to keep the company alive.
Selling to legal organisations is tough. Lawyers are hard buyers. They’re perfectionist, sometimes pernickety, and quite all or nothing in their buying mentality. Even if a product is amazing, and far better than the cost of doing nothing, sometimes a sales cycle can fall apart for very trivial reasons such as the product’s workflow not matching 100% the exact way of working the users at that particular firm in that particular team do their work, even if overall it is 95% a fit for them and all others in their niche. And that decision might come at the end of an 18 month sales cycle.
And as you say, that holds true for the big players like Litera, who you joined after dealWIP wound down.
How did that move come about? What transferable skills did you carry across from your prior experiences into the Litera role?
I was really blessed, first of all, to get that opportunity.
I missed ILTA that year. It would have been embarrassing to show up knowing that we were going through that process at dealWIP. We had to let go of five employees in our office in Nashville, let all of our contractors go, and my co-founders returned back to work.
And one of my best friends (Zach Croft) sadly passed away tragically during the same stretch. It was a period of real darkness for me.
So, that’s what I did. Everyone knows Noah sees around corners. And, everybody that knows Avaneesh Marwaha knows that he’s one of the most casual and down to earth people around. He’s not what you think you’re getting with a private equity-backed CEO. When he jumps on the line, he’s like, “Hey, what’s up?”.
He calls me up and I thought, “this is going to be OK, I can talk to this guy”.
Before the call I was afraid because I thought everything hinged on it. I thought this would be our chance to sell dealWIP and get something out of it for our investors and that weighed heavily on me, in terms of coming to terms with the heaviness of the nearly million dollars we’d been entrusted.
We started talking about how due diligence project management – what we’d built dealWIP around to that point – was an obvious on ramp to transaction management technology, of the sort for which Litera is now well-known. Things started to make a lot of sense, we could see what each other were doing, we continued talking and I started speaking with the Chief Product Office at Litera, Jason Vander Meer, and vibing… and I thought “wow, we’re going to get sold after all”.
But long story short, it didn’t work out that way.
The deal just didn’t make sense for Litera at the time. And having been inside the company now, I completely get it. They were integrating Workshare Transact and Doxly, which was the focus, and was a behemoth of an effort in and of itself.
So, we sat down and broke bread.
Anybody that knows Haley knows that she’s a force of nature. She’s really good. She has singular focus. So when she described what she was after in her new role, it jived with my ambitions and vision, and I saw a role for myself and she asked me to join and head up strategy for the Transaction Management product line at Litera.
And I thought, “are you kidding me? I get to do the same thing I was doing at dealWIP, but with access to unlimited capital. Yeah. I’ll, I’ll take that!”
It was very fortuitous. I got to work remotely as well, so that was great because my wife and I got to move back home to Maryland from Brooklyn, which was when we also learned we were having our first child.
It was just perfect timing; returning home, having a job that was flexible with access to capital and starting a family. It was just an answer to prayers.
Right place, right time and right network?
Absolutely. I’d also like to highlight Avaneesh, and of course Noah and Haley, who extended me a timely opportunity. They each saw what I’d done and what I wanted to achieve, and found a way to put me in position to shoot my shot. From there, it’s all about wanting the ball. And, I always want the ball. I love to shoot.
Network is so important. It’s a lot easier to build a strong network if you are genuinely excited by the domain. One thing we’ve found about the legaltech market is that networking seems very easygoing, natural and supportive. For the most part people are very open and authentic about sharing their war stories as well as their successes. It doesn’t feel forced as say legal or finance networking events where it’s perhaps less like that on average.
That’s right, I think. It’s great to not need a happy hour and a bunch of drinks to drop the corporate mask and be real and admit that you don’t really want to talk about the nuts and bolts of a rather dry legal or legaltech topic, but instead want to get to know the person and what made them happy or hurt them that day.
We’ve covered a lot already but what tips would you recommend to people, at any stage in their career, thinking of embarking on a change, whether it’s from law into politics, tech or starting a business?
Number one is this, and I’m fretful about saying this because I don’t want to come across in the wrong way, and lose people. But in all earnestness, and it will mean different things to people: talk to God. Talk to your God, whatever or whomever that is. God is real.
For me that means going inward, slowing down, and really thinking about what moves me. Don’t be a thermometer, arbitrarily adjusted by others’ energy. Try to be a thermostat if you can, intentionally adapting to what truly moves you rather than letting other people’s notions of success drag you this way and that. And, the only way you can do that is to understand the power of heat. If you don’t understand heat, you can’t take control of the temperature.
Number two, seek wisdom. But be careful to whom you talk. Because not everyone knows what they’re talking about! And not everyone necessarily wants for you, what you want for yourself.
Number three, develop a disciplined and structured way of evaluating your go-forward path. And what that means to me, is allowing yourself to freestyle. Play your jazz chords, but also understand the mathematical rigor with which traditional orchestral arrangements are constructed. Blend those two worlds artfully, and one can produce real magic in the world.
In more concrete terms, that means systematically de-risking your opportunities.
Try to understand your invisible assumptions and try to validate those first before making a move that will put you at unnecessary risk or have an adverse impact on those around you. Don’t take risks just to take them because it feels good. Try to do it in a responsible and sustainable way.
Number four: be honest about the outcome of your experiments. Don’t tie yourself too closely to any idea. Your idea, your experiment doesn’t have to win. You don’t have to be the CEO. You don’t have to be a lawyer. You are because you are, and your results are what they are. Separating your results from your identity allows you to play with lots of things, because they’re just things – they aren’t you. Your legal education is a thing. Your career at any given point is a thing. But it doesn’t define your identity. Play with those things to make your life fruitful and make it interesting, try to learn and to bring other people close to you because that’s where we find joy.
The last thing is to seek truth. Once you honestly set your mind on seeking truth, even if the truth ends up being different than your ideas or what you perceive to be your identity or the value-set native to your tribe or your people, it sets you free and gives you the kind of peace and insight that will surpass or evade common understanding. In that, there is tangible opportunity – concrete commercial opportunity, but also spiritual freedom.
And I want to be clear here.
Seeking truth, and being true to yourself, are two different things.
Talking to your God allows you to be true to yourself. Your God knows who you are.
Seeking truth is outside of yourself, because what is true for you is not necessarily true for your neighbor. So when I seek truth, in a sense I’m looking for what’s most true or most relevantly true in a given moment.
For example, if you tell me that I make you feel awful and if I am saying to you, my God tells me that the way I treat you is the way I’m supposed to treat you, there’s some dissonance there that’s going to cause you suffering and also cause me suffering.
In that scenario, the truth I need to seek in the moment is what you are telling me, because if my intent is good, is to live in harmony with my neighbor and the people around me, the most relevant truth at that point is how I’m making you feel. And that requires humility, character and discipline. It requires you to quiet your ego and look for what matters.
You are now the co-founder of ShareThing. Appreciate this is a very recent venture, but is there anything you can share?
Let’s not spend too much time on that because that’s very new, and I don’t want to tell a story before it unfolds.
What I can say is that the love, the trust, the truth, the growth, and not worrying so much about things, and worrying instead about the people, is where ShareThing is coming from.
It’s this idea that what’s more important than anything are the meaningful connections between humans and not so much the material things that we’ve come to worship, whether that’s our careers or our cars, or our third monitors (lawyers know what I mean).
Those things are only good in so much as they bring us closer to realizing that we are really connected to one another in a deeper way than we could even imagine.
That’s the cool thing about ShareThing. It’s based and built off something that pre-existed me. It’s a genius idea that I had nothing to do with, the buy nothing project. There’s lots of literature out there on what that is (see here).
It’s a beautiful concept. Unincorporated free flowing organization, more of a movement. It’s about creating distributed hyper-local gift economies in which the true wealth is the web of connections formed between people who are real-life neighbors, who share.
There are already 3 million people involved globally, spanning 44 countries. The movement has over 6,000 hyperlocal sharing groups, and is growing at nearly 230 groups a month. In January 2021, the movement trained the most people ever trained in a month to be administrators or host these groups. Before January 2021, the previous record was 250 people trained, and in January 2021 the movement trained just under 2000 new daily volunteers.
We’re seeing this inflection point globally, and the size (and rate of growth) of this movement is awe-inspiring. We think it’s the right time to build a social sharing platform. We see really heavyweight competitors going into this space and trying to gain ground.
Facebook is beta testing a Neighborhoods feature, which is based around ostensibly similar ideas. It’s something they want to make core to their platform later this year. They’re testing that in Canada right now – a country where the Buy Nothing Project has a large and rapidly-growing community foothold.
Another company, called Nextdoor, is currently valued at $2.2 billion and may shortly go public and aim for a valuation of $5 billion this year. They have 27 million users. It gives you a sense of the value of the Buy Nothing Project community – already at 3 million users, with zero marketing.
And then you also have Amazon Neighbours, another similar initiative.
But no one in the space has as strong and trusted a brand as the Buy Nothing Project. It’s a beautiful opportunity that comes with immense responsibility. My co-founders and I have to steward and protect the integrity of the community and the brand. It’s way more important than money. It’s too important, to too many people, to squander. We’ve committed ourselves to building this business thoughtfully and with conviction, at every stage. We’re dancing to a different tune with ShareThing.
It’s all part of this emerging idea of connecting with people where you live that’s about to take flight, and we happen to be in the right place at the right time and want to build a brand with integrity around bringing people together in meaningful ways in the physical world.
So many of the material possessions we all stash away in our homes essentially function as options on things that we might enjoy one day, sometime in the future, or maybe never. Those are potentially valuable things somebody else could enjoy right now, in the present. We should be moving these things around, sharing them via our personal and community networks. It’s a beautiful idea. We have the technology to make it a global reality, in every corner of the world. That’s what we’re doing at ShareThing. It’s a massive undertaking. A very long-term journey.
That sounds really apt. Especially as everyone has had to pull together more in the recent tough times we find ourselves in with a global pandemic. That and other headwinds such as environmental concerns seem to be driving more neighbourly connections.
Lastly, do you recommend any books, podcasts, blogs or social media to check out, things you’ve found helpful to your career and life decisions?
I’d definitely recommend:
- The Knowledge Project podcast by Farnam Street. This is a great podcast about better thinking, problem solving, and decision making. I’ve learned so many great insights about how to think better from this podcast. Well worth your time.
- Venture Deals: Be Smarter than Your Lawyer and Venture Capitalist by Brad Feld. A must-read for anybody trying to start a business and negotiate with sharks!
- The Lean Product Playbook by Dan Olsen. This is a great resource on lean product development. I learnt everything I know about product from this book. It aims to bridge the gap between The Lean Start-up and how those principles apply directly to building great products. It walks you through a lot of practical examples and a repeatable, easy-to-follow methodology for iterating your way to product-market fit.
- The Buy Nothing, Get Everything Plan by my ShareThing co-founders, Liesl Clark and Rebecca Rockefeller. It documents their journey from 2013, when Liesl and Rebecca launched the first Facebook Buy Nothing Project group in their small town off the coast of Seattle, which unexpectedly became a viral sensation. It’s a great read on discovering the joy of spending less and sharing more and living generously. Very inspiring.
- The Revolt of the Public and the Crisis of Authority in the New Millennium by Martin Gurri. This is a great read about how technology has reversed the information balance of power between the public and the elites who manage government, political parties, and the media. In doing so, Revolt of the Public tells the story of how insurgencies, enabled by digital devices and a vast information sphere, have mobilized millions of ordinary people around the world to challenge the status quo.
Finally, I have launched www.tunjiwilliams.com, a personal project to explore many of the themes that came up in our discussion through various of expression: visual art, photography, original music composition, poetry, etc. I hope you enjoy it!
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