Presto Magic

Part 1

In the spirit of honesty, I’ll provide a few of my reasons for why I came forward in the first place. First, I felt called to do so. One of the principles I committed to as part of my Personal Credo Journal was “I tell the truth to others and myself.” Honesty was (and is) a deeply-held aspirational value. I like to be All-in on things in my life. Once I decide something is worth doing, then I go All-in on it. One of my mentors once observed that I’m a “man of extremes.” I’d classify that as an accurate observation. I prefer to live my life this way. All-in or All-out. Hence why I pour a lot into deciding what I want to do (and who I want to be) at the beginning. Because once I’ve decided, I’ll pursue something with all of my attention and energy. “Balance” has a different time horizon for me. Whereas some might aim to create balance on a daily basis, I might create it over the course of a week. The same goes for months and years. I worked hard for 5.5 years making money (not including the years of dedication that put me in a position to land the job in the first place). And then, for the past 12 months, I’ve been enjoying a money-burning retirement. But, I digress… All that to say, I like to be All-in on things in my life. In the Spring of 2024, I asked myself the difficult question of “What are you All-in on? What are you solving for?” Honestly, I didn’t have a great answer. What surfaced initially was “Honesty.” But what followed behind this initial thought was “No you’re not.” I did my best to ignore this retort. But then, this voice expressed its disagreement again. “You’re not All-in on honesty. You lie on your expense reports on a monthly basis. How could you claim to be All-in on honesty when you’re consistently, consciously lying?” This was a hard truth to hear, but it also catalyzed a fundamental change in me. Once I heard it and once I felt its relevance, there was no more denying it. Any time I’d state the claim to myself, “I’m All-in on honesty”, I’d be met with the voice of that pesky lil truth-teller, shouting from behind my ears, “No you’re not. You lie all the time. You’re not All-in! You just tell the truth when it’s convenient.” This led to more frustration than I’d previously thought possible. Extreme frustration because I began to realize that it was possible for me to consistently and consciously lie to myself. I realized that I was living a lie. I was living a lie because I was telling myself I was one thing, yet living another. I believed myself to be an honest, aware, discerning individual. And yet, on a monthly basis, I was lying on my expense reports, then I was convincing myself that I wasn’t (or, at the very least, that my lying was justifiable). Despite prophesying the importance & value of truth-telling to anyone who would listen, I was living something completely different. I was making the case to myself on a monthly basis that I couldn’t trust the truth. Or, at least that I couldn’t trust the truth all the way. So, I found myself in that most-miserable state of misalignment. I knew the truth, but I was living something different. After making this recognition and stewing in my miserable misalignment for a couple months, I confronted another hard truth: I had the power to do something about it. Up until then, I’d “successfully” convinced myself that I didn’t have any ability to change the situation. I told myself, “Sure, I could stop incurring questionable expenses, but I couldn’t do anything to change the past. What’s done is done. I made mistakes. At least I’m admitting that to myself now. But there’s nothing more I can do to clean up the mess I’ve made. I can’t go back and reverse the damage.” And yet, this line of thinking still wasn’t sitting right with me. I still found myself swimming in a pool of misalignment-induced misery. I still felt disconnected from the team. There was still a secret that I was afraid would eventually be exposed. So, I found it difficult to open up completely to my colleagues… or to myself. I found it difficult to fully open up because I was afraid of a slip up. I always had to watch my words because if I said the wrong thing at the wrong moment, then I might give away my secret. And if I did that, then everything could come crashing down in an instant. (I know this all sounds a bit dramatic, but the master-destroyer, Anxiety, has a knack for doing that.) So, it was equal parts frightening and empowering to confront this previously-buried, but now-surfaced truth, that there was something that I could do… I could come forward and tell the truth. Granted, I wanted to be thoughtful about who I came forward to and how I did it, because I didn’t want my truth-telling to inflict any collateral damage. As I strategized about how to do this, I realized zero collateral damage wasn’t going to be an option. I would have to tell somebody in order to pay back the money. Otherwise, if I wired money to the firm for no apparent reason, then somebody would eventually start asking questions (presumably). Then, I’d face the choice of 1) telling more lies and separating myself further from the truth or 2) getting this unsuspecting, but now-suspecting, individual wrapped up in my situation where they would then face their own dilemma regarding Standard Operating Procedures. So, I decided to come forward to the one person who I believed would have to find out eventually. One of the firm’s leaders, who, I believed, had consequential decision-making authority. I admitted my mistakes to them. I apologized. I expressed my remorse for breaking their trust and the trust of the entire team. A team that I saw as a second family. A team that had given so much to me. I told them I would pay my restitution. I even offered my resignation, if that would make the whole situation easier on them. If the firm wasn’t going to accept my payment or if it would create issues with balancing the books, then I told them that I’d be sending it anonymously to charity. The number that I shared with them was intended to be overly-punitive on me. Any expense that could be remotely considered as being “in the grey area,” I included in the count. Because, as I ran the investigation on myself, I wanted to do it justly & fully the first time around. I was self-reporting my own mistakes. An extremely vulnerable, gut-wrenching, ego-threatening task that I didn’t have to do in the first place. So, what would be the point of holding some expenses back? If I had more to hide, then why would I simultaneously erode the trust that people placed in me and shine a spotlight on my misgivings? If I had something more to hide, then what would be gained by increasing other people’s suspicions that I’m a criminal? Why come forward and admit my mistakes, while also offering my resignation? If I had something more to hide, then why not just walk away? Why not walk away and say that I wanted to take a Sabbatical? Why not collect my pro-rated, almost-half-a-year’s worth of VP bonus, along with all of my deal & fund carry intact (carry that got wiped to zero when I was fired for “serious cause”), while departing with a “job well done”, a “thank you for your service”, and a round of applause? At the very least, why not wait a couple weeks until I got paid a bonus — that would dwarf the amount of the questionable expenses — for sourcing a portfolio company that had just been acquired three weeks earlier? Why? Why? Why?!? Because, to me, it just didn’t feel honest. I’m not a masochist. I wasn’t seeking maximum punishment. That’s why I came forward to the one person I who knew would have to find out eventually. I thought we could rectify the situation together, as a team. But instead, they chose to go with the Standard Operating Procedure. I didn’t want this to become a big thing. I was deeply ashamed of what I’d done. But I knew I needed to tell someone. And I knew I needed to pay back the money. That’s what I knew I needed to do. I knew it was a selfish decision, but I preferred to see it as True Selfish, especially because it was in service of my core intention of honesty. My decisions won’t make any sense to someone who’s solving for money. There’s so many other ways I could have played this situation that would have left me walking away with far more money than I have today. After the firm’s lawyers informed my lawyer that the extent of the questionable expenses “could be as much as $70K”, then I knew I was right back to facing my dilemma again. Only this time, it was with higher stakes. Did I know that this $70K was more of a threat than substantiated with evidence? Of course I did. And did the size of this threat make me even more tempted to hand over my personal phone and show them that I had nothing to hide? Yes. Was I tempted to hand over my personal phone, along with a whole host of text messages and notes that would expose the truths of the people who were conducting this intimidation-driven investigation? Absolutely. The poetic justice was exceptionally tempting. But I also knew that exposing their truths would be satisfying for about a second. Then, the fallout from these revelations would create very real damage to the entire firm and its reputation. Even though I made multiple pleas to many different “mentors” and “friends” to simply sit down and have a conversation so that I could explain the gravity of what they were asking me to do, even though I was fired and disgraced by the people I was trying to protect, I didn’t give in to these temptations because their truths were not mine to share. They shared these truths with me in confidence. Instead, I wired the firm $70K and I walked away. Even as their lawyers informed me that I’d be sued in court for access to my personal phone, I told the leaders of the firm, which I used to consider a second family, that I would be willing to meet with them 1-on-1, in-person whenever they were ready. I offered multiple times to tell them my side of the story. I just wanted to share my reason for doing what I did. And I also wanted to share that how what they were asking me to do was not in their individual best interests. I didn’t want to expose them for what they’d shared with me. What started as a desire to right my relationship with them by owning up to and paying for past mistakes I’d made, what began as a desire to be honest and not keep secrets anymore, came into conflict with another personal principle of not exposing other people’s truths that were never mine to share in the first place. I know how hard it was for me to admit this truth to myself. I know how much harder it was for me to come forward and admit this truth to another person. And I know the depth of the betrayal I felt when I’d learned that this person had told someone else without my consent. Even though my rational brain knew that this individual was just following Standard Operating Procedures and had a whole host of reasons for doing so, I was also holding out hope that we would be able to work towards a solution together. In hearing that they told somebody else without my approval, I felt betrayed & defeated. Like my trust in this individual was worth less than the information that I’d just provided them with. The currency of the information was valued more than the currency of our trust. Again, I understand why this individual did what they did. However, after reviewing my own emotions amidst this situation, I knew that I didn’t want to be a part of perpetuating that cycle. I didn’t want to break my own principle of privacy because the Standard Operating Procedures told me I was supposed to. Even though the lawyers threatened to take me to court and publicly decimate my already privately-destroyed reputation, I wasn’t willing to trade who I wanted to be for something that somebody else wanted from me. Yes, I knew that I was protecting the people who were threatening me. And yes, I knew that I was protecting the firm that kicked me to the curb without listening to my side of the story. And of course, I knew that wiring this massive company $70K would mean nothing to them but a whole heck of a lot to me and my hypothetical future family. But, I also knew that this was a great opportunity for me to see if I was really “All-in on honesty.” Rarely, are we presented with opportunities where we get to put our principles into practice. Rarer still are the times when we get to do so when there’s a very real risk of very real consequences. So, here we go again. I’m writing this on the 1-year anniversary of being unceremoniously & un-in-person-conversationally fired from my previous family. Up until now, I’ve held back sharing this truth publicly because I haven’t wanted to expose anybody else’s truths. Again, adhering to my own principle of privacy. But, I’ve also come to realize that sometimes there’s situations where two principles come into conflict with each other. When that happens, the best I can do is to try to minimize the collateral damage of the path that feels most honest. I have no intention of outing anybody who I used to work with. Like I said, I understand that they had their own reasons for doing what they did. I look forward to hearing specifically what they were if they ever choose to speak to me again in-person. I’ll continue to protect their truths that they shared with me back in the day. But, I’m no longer afraid to share the details of my own story. I’ll do my best to minimize the collateral damage, but this is my truth. This is my lived experience. This is my story. And I earned it. So, here we go again… if you’re still wondering what I’m solving for, it ought to be obvious by now. For me, it’s all about honesty. And I’m All-in.

Part 3