Best/worst career decisions you’ve made?

I worked in finance in multiple industries, that gave me an advantage for recruiting later in my career. better network also.

Staying too long at a place that paid more, but really fucking sucked. Toxic environment, walking on eggshells, micromanaging, etc. basically a sweatshop. These days I'll gladly take a pay cut if it means avoiding bullshit like that. 

I have always prided myself on being transparent, for better or worse. My first job out of school was risk at a large utility. Like my fist couple months in, it was well known I wanted to trade. I was tight with a few of the senior traders, a director had kind of taken me under his wing and roped me in on a few projects. My boss was cool with it, his boss was not, not even a fucking bit. ‘I would have never hired you if I knew you wanted to trade.’ That was the beginning of the end, like four months in…. I stayed for another year, then left for a trading role. That was a miserable fucking year.

Still to this day, I have stepped on my dick due to my transparent nature, but unfortunately I’m not able to keep my cards close to my chest, I prefer to just be open with my intentions.

Probably starting my career at big 4 in transaction advisory. No bigger professional scam in the world

Have a few best career decisions:

Sticking it out with my pre-MBA job. I really enjoyed my company's culture and I got great managerial exposure. Pay eventually was above market (I was definitely underpaid when I was initially hired) but it was a boring repetitive job in an operational role. I barely did any work after I got into my MBA programs and my direct boss never noticed. When I was an entry level hire, I absolutely hated the job and almost jumped to a 'more intellectual job' that paid the same but had higher stakes (aka I had to produce results almost ASAP). My pre-MBA job had a lot of mindless / repetitive work (worked in healthcare and many of my standardized workflows had a direct impact on care delivery for thousands of patients). Had one or two department projects I led where I was able to be creative but those were short lived, rest I had to go by the book / protocol.

Prior to joining my last job pre-MBA, I almost made the switch to CPG / fashion which was right before COVID after talking to a family friend who was a public co C-suite. My background is completely irrelevant to CPG / fashion but I was in a desperate job search. He politely denied to hire me and he probably saved my butt since COVID hit months later. Pretty sure his company had mass layoffs.

Moving out of audit before I qualified for my CPA. Used to be unconventional and looked down upon but is happening more and more frequently. Old senior told me I dodged a bullet because our client is rough this year and so far new job in corporate finance has also been busy but it’s still more interesting than before and the hours should gradually get better. Managers can be a bit more hands on and provide some more direction in my opinion but otherwise team is solid and got a nice raise from this. We really don’t get paid enough to work the hours in big 4 in Canada though…

Stayed (almost) the full two years at my first job out of UG. I remember at the time it felt like an eternity, and I wondered if I would ever move on. When I did eventually leave, it was to stay in consulting but work at a better firm in a better group and with a more senior title. I honestly got lucky that I found an opportunity to improve title / comp / prestige all at once, but looking back on it would have jumped for two of the three criteria. The reason this mattered so much was that later on in my career I jumped around a lot, but was not perceived as a flight risk (at least to my knowledge) due to a couple strong years at my first company. 

Biggest mistake? I rolled the dice on joining a very lean and disfunctional Corp Dev team. I was eager to get into corp dev and it was the only offer I had and I kept getting beat out by kids with IBD backgrounds so I took it and counted my blessings. While the job sucked, it allowed me to learn the fundamentals and lateral to a much more sought after role. It was the equivalent of joining a smaller LMM boutique and eating shit in terms of hours and comp so that one day you could lateral to a strong MM / BB. 

To provide some general (hopefully) helpful advice, screen the shit out of any place you work at that isnt well regarded. Looking at Goldman or MS, you know what to expect. But what about some PE fund with 200 MM AUM and 10 employees? My general advice would be that you need to cover all your bases in your interviews (what are hours really like, how much is WFH, opportunities for advancement) and address those semi-uncomfortable questions. Further, upon receiving an offer, you need to do you DD and ensure you have covered everything that matters to you. They have an office in Houston but say you can WFH in another state? Get it in writing that you wont have to move for the job and / or will actually be able to work remote say 75% of the time aside from mgmt presentations and site visits. My biggest regret was starting a job that told me x when in reality it was y, which made me lateral very very quickly and leave with a bad taste in my mouth.

I started my career in corporate but at a couple huge companies in my industry where development/opportunities were measured in decades not years. Jumped over to do sell-side equity research at a niche bank for 1) higher comp but also 2) more senior level exposure at coverage companies. Realized very quickly that the boutique ER model is not for me but fortuitously got recruited to go be finance employee #2 at a portfolio company of a well-known PE shop 4 months after I started my ER gig. Didn't love the idea of leaving after 4 months but made the leap....1.5+ years later, I've been promoted twice, have learned the equivalent of what would've taken me 10+ years at any of my other gigs, and really feel as though there is a senior leadership position awaiting me within the next 4-5 years (I'm <30 y/o at the moment) if not at my current company than at another portco of the same PE shop. Best decision I made was to throw the middle finger at the ER gig and take this chance.  

So I'm at an O&G portco, and O&G PE is a little different than traditional PE in the sense that the PE shops aren't buying existing assets/businesses. The strategy is to commit dollars to a management team to then go out and build a business/asset. The PE sponsor's level of involvement 100% is dependent upon their relationship with the management team; an unfavorable relationship/being on the sh1t list of the PE team and they will be a lot more hands on in the day-to-day. In our case, our management team has a strong track record with the PE shop and this is actually the 2nd iteration of the company (the first had a very successful exit) and thus they are pretty hands off. Thus my role is very much that of a true corp dev/corp finance person in that we are running our entire A&D/Capital Markets strategy in-house. 

All that being said, every single one of my peers at the other portcos have unique experiences. I was very fortunate to join a strong management team combined with a boss (the company's CFO) who is eager and willing to delegate responsibilities to me as I've grown. Others without that relationship or with less than stellar CFO's have not had the same experience. 

Regarding pay/comp....again varies by the individual portco vs. being a broader industry thing. The differentiator is the level of equity in the company since the goal here is a monetization event (either sale or going public) which if executed well can be very lucrative. 

For most of my peers and myself, it was part of the initial comp package. Most of my peers (myself excluded) were ex-IB Associates (or in some cases VPs) so cash comp won't be anywhere near what they were making in their prior life, but with the tradeoff of a much much easier lifestyle. So to bridge that "gap" the companies almost have to provide equity to make it worth the transition. You still will probably end up net-negative on a comparative basis, but probably not drastically over a long enough runway. 

Whatever that initial comp package is though doesn't mean that's all you will ultimately get. I.e. I have a peer who was brought on as the sole Finance professional (title was VP of Finance but day to day was essentially CFO) which worked when they planned on a sale but when the sale process fell apart and they reconfigured to hold the business for longer, they intended to bring in a more seasoned CFO from outside of the organization. For the VP, he now had a formal boss so to compensate that he got more equity put into his comp package. All that is to say it is very fluid and everyone's package varies, but because the cash component is usually relatively lacking, it is almost always built into the original package.