Inspired by the recent return of some all-time great WSO members, we will begin featuring a series of posts from forum favorite 'superusers'. This "Then and Now" series will let people share a bit of their story through a handful of questions that touch on their career progression and how this site has supported that.
When did you first join WSO?
I started browsing and learning in late 2013, but it was a while before I started commenting & contributing. I managed to get all the way through school without ever having touched a business course or concept, and by this time I was trying to get up the learning curve in my investment banking stint. WSO had a lot of answers to questions I couldn't seem to get answered either by my colleagues or from other sources. That led into broader conversations about career paths and some camaraderie that I really enjoyed.
Why did you join?
I was hungry for a community that thought about and cared about the same things I was trying to explore. I didn't have any friends who worked in investment banking (save my colleagues, and it would be a stretch to call them friends). I didn't create meaningful connections into the industry when I was in school, since I am a natural introvert who was nose-deep in engineering coursework and trying to balance that with the demands of NCAA athletics. At this point, I didn't have anyone I could ask basic questions of.
Where were you in your career then?
Getting my teeth kicked down my throat as an investment banking analyst. Even today I find myself sometimes avoiding diving into a model or working on slides, even for a personal project I'm excited about, because it brings back a lot of negative memories of work I hated and people I'd like to forget.
Where are you in your career now?
I'm a VP in the capital arm of a merchant bank. Most of the work our firm does is traditional boutique investment banking - solving capital structure problems for middle market business owners. Debt placements, recapitalizations, minority equity sales, exits. We do some buy-side work too. But we have a capital arm that can place creative equity into special situations, which is where I spend most of my time. It's very non-vanilla, which means I only look at things that have weird valuation methodologies and/or payback structures. If there's a good business for sale represented by a banker and looking for a 100% buyout, I'll be nowhere near it.
I'm fairly autonomous in my day-to-day life, so I haven't had much heartburn over micromanaging since we've gone home-based. But anything we do is subject to an investment committee that holds final say.
Looking ahead, I love what I do and the situations I get to be a part of. I haven't butted heads much with our IC about deals, so as long as that's the case, I'm inclined to keep doing what I'm doing. If we ever diverge, though, then I'll likely split off and hang a shingle.
As an aside: I'm big on alignment of autonomy and responsibility as a delegation paradigm - in other words, if someone is responsible for (measured on, compensated on, etc.) an outcome, then they need to have autonomy over the process by which that outcome is achieved. If someone doesn't have the skill set to have autonomy over a project or a task, then it's unfair to give them ultimate responsibility; and if you delegate an outcome, then you have to also delegate the process. A lot of battles between management and subordinates come from a disconnect in this concept. Ever since I realized this framework, I've been really sensitive to missteps, and as a result, I really struggle to work for anyone that doesn't share my worldview.
What can you share about your personal or family life?
Married, offspring, that's about it.
If you passed me on the street, or walked by my house, you'd never guess what my career path is or what I do now (or what our combined income actually is). I'm a pretty private person, and it's hard to describe the relief it gives me to not draw attention to myself. My dream is to have a quiet house in a nice neighborhood and have a portfolio of companies that throw off more cash than I'll ever need, and none of my neighbors would ever have any idea. Some of my best friends are people that I met in elementary school, and I would like to keep it that way.
Looking back on your career, is there anything that you thought you knew starting out which turned out to be wrong?
Just about everything. My vision of what I thought I wanted when I was 25 was absolutely nothing like what you see above. I had always known, on some level, what I wanted my life to look like - but it seemed like my immediate circle and society tried to beat that vision out of me. So I did what most 25-year-old recovering athletes did, and I worried about making money and showing others that I made money, and I worried about my body count, and I worried about what my bosses thought of me, and I worried about if I was behind on buying rounds at the bar, and I worried about all the things that are a straight ticket to being unfulfilled with your life.
I remember my first month at business school, I was on edge. I was going to show all of these mouth-breathers how I could out-think circles around them. I remember an alumnus who came to talk about his business - after spending seven years post-MBA at McKinsey, he had left to start his own practice (doing something, I don't even remember what). He was making about a fifth of what he had been and he said he couldn't be happier and wished he had done it sooner.
I thought, "what a fucking loser." I was sure that he was protecting his ego by convincing himself it was okay that he hadn't made partner - that he had failed. My tunnel vision for what I thought everyone's career goal needed to look like was crippling.
So I accomplished what I thought it meant to "win" - I got into a private equity role from a business school outside of H/S/W, I had the highest annual comp of anyone from my graduating class, and I did it. I won. I showed everyone how much better I was than they were. I reached my mountaintop.
And it was empty. Turns out I was satisfying someone else's picture of what a successful life should look like, not mine. The great name on my business card and the social recognition and the validation just didn't add up to what I thought they would.
Lucky for me, I've found a role that allows me to live my life the way I want to live it, while working on interesting things, and making a comfortable living for me and my family. Had I known at 25 that this is how I would find happiness, I would have taken a wildly different path (and probably could have gotten to a different solution without so many twists and tangles). But who knows, maybe it's the path that showed me what I really wanted.
Were there any opportunities that presented themselves along the way that you didn't take? With the benefit of hindsight, do you wish you had taken one of them?
Just a couple. There's an opportunity that I could have taken out of business school that in retrospect, would have been a great fit for me, but I couldn't get myself to take it seriously because it wasn't a private equity role. Knowing what I know now, I would have at least given it a shot.
I also passed up a threesome in high school because I was too chickenshit to recognize that these girls were into me - it was much easier to live under the protection of "not being in their league." It took me about five years to realize what had happened. Shoot your shot, guys.
What do you think has made you successful in your career? Are there any particularly interesting or unique challenges that you've faced along the way?
This one is a double-edged sword, as the thing that has been the greatest source of my success has also been a hindrance in plenty of situations.
Put simply, I'm a truth-seeker. I have a sometimes-unhealthy need to find out the truth at the heart of something. It's a benefit when the goal of a group is to find what's really going on - at a company level, or at a scientific level. I often have people get frustrated with me because they think I just like being right. They're correct, kind of - I like to have earned being right. I have no emotional attachment to a position or an answer, and I'm happy to be proven wrong. If someone comes along with a better argument, then ... now it's my argument! But if someone presents an argument or a poorly-structured sequence of facts and gets frustrated when they don't change my point of view, that's when it stops being fun.
It's been a challenge because not everyone is incentivized to find truth. If there's a guy that isn't very productive at work, but is a great personality that can win any board meeting, then it's not in his best interests to institute more transparency and accountability in tracking work initiatives. If the real answer to a question you're probing someone on is "I don't know and I didn't take the time to think through how to find the answer," and they're afraid of saying that, then they're going to feed you some bullshit to send you in a different direction. I have had a lot of difficulty in my career in working with people and in organizations that don't value truth and honesty the same way I do.
It's why I like weightlifting so much. There are no style points in weightlifting. 150kg is 150kg, anywhere in the world, any time of day, same as it was yesterday, same as it will be tomorrow. Success is binary, and whether you make the lift or not, no excuses or explanations are needed either to an audience or to yourself. The iron doesn't lie.
Is there anything else you'd like to share?
I am indebted to this community. Someday I hope to have given back as much as I've gained from it. I have a long way to go.