Category Archives: Wall St transition

From Wall St. to Start Up St.


When I tell folks that I transitioned from an i-bank to a growth stage start-up, most ask a number of questions that sum up to “well, how is the start-up thing?” Such conversations have inspired me to write a post documenting my thoughts on the matter. While this is not a thorough analysis of all the considerations involved in making a move from Wall St to Start St, it is certainly meant to draw a fair comparison between the two worlds on what I believe to be several important points.

1.       Work-life balance. “Face time” really matters in finance. My roommate is a mid-level associate on Wall St. and she still never leaves the office before her boss. I am happy to say that my current company isn’t as plagued by a “how-many-hours-was-your-b*tt-in-the-seat?” culture as most on Wall St. I am not suggesting that I clocked out at 5 pm on my first day. Like in any new job, there was an initial period of proving my worth and building my boss’ confidence in my work ethic. However, once I felt that this had been achieved (she wrote me an email complimenting my work ethic after two months on the job), I have not hesitated to leave at 5 pm if I have another appointment occasionally, or for coffee with a peer at noon. Having a work laptop that I carry everywhere, something I didn’t have in finance, has been a huge help in ensuring that I don’t take advantage of this newly found flexibility at the expense of my workload. I am sure to make up whatever work time I miss during the day at home, in the evenings. As a result of this arrangement, I work a comparable number of hours at a start-up, but have a significantly better work-life balance because I feel more in control of my schedule. It certainly helps that my current company’s office is in a prime mid-town location with lots of stores, restaurants, and in close proximity to organizations that I am involved in outside of work, instead of being in the middle of nowhere on the west side of the city!

2.       Co-workers. I am going to be painfully direct on this one. Some of your co-workers at a start-up will not be of the same caliber as your finance colleagues. They will submit work to you that will, unfortunately, inspire you to ask if the assignment has been given more than 10 minutes of thought. Some of them will also not have the same level of erudition, worldly knowledge, or put in as many hours as your i-bank colleagues. But they will likely be a lot more relaxed, helpful, cordial, and appreciative of good work because the baseline standard is lower. For better or worse, my current company is sustained by a handful of A+ players who are brilliant and give their work 150%, which, in turn, allows others to put in 70%. I constantly find myself thinking that if the other folks gave it, at least, 90%, we would be so much further ahead.

This arrangement has pros and cons because while the caliber of my colleagues at the i-bank was higher, I had to quickly learn the swift art of covering my *ss. Before I could turn around, I was lying under the bus covered by tire marks at the i-bank. The blame games and finger pointing haven’t happened nearly to the same extent in my year of employment at the start-up. It was difficult not to succumb to the pressure of a super competitive environment on Wall St. On Start Up St., the professional atmosphere isn’t as intense; no deadline feels as pressing (I know this because I have missed a few, without any material repercussions). Colleagues are not at each other’s throats, fighting to be in the top quartile of an analyst class or for the small, finite number of promotions. For example, when I first got to the company, I sent an email that wasn’t in line with the company’s culture. A colleague pulled me over and quietly let me know. In finance, most colleagues would’ve let it sit there and waited for me to repeat the mistake. I say thank g-d for nicer, but less professionally intense people. Pick your own poison on this one.

3.       Impact, work content & pay. I feel that I’ve been able to have an impact on my current company and its employees in ways that would have arguably taken me years at the i-bank. In finance, especially at the analyst and junior associate levels, I felt three degrees removed from the real-life impact of almost any transaction that my team was working on. At the start-up, I built a system that the entire company has transitioned to in the past year and that is integral to each department’s strategic plans for the future. In building this system, I have also made design and tech decisions that have been, without a doubt, over my head. To do so, I’ve had to do research, ask a lot of questions, and interact with folks in positions whose counterparts at the i-bank I never had exposure to.

However, because there are less folks to work on anything at a start-up but tons of work to do, I have found myself part of “all-hands-on-deck” situations where I am executing on menial tasks. Even still, at the start-up, I feel that whether big or small, the work I am doing is part of a movement. The company I am part of is charting a path to something better and more innovative (in this case, it’s a better way for employees to buy benefits) than what exists; it is working to improve the status quo and I am at the forefront. At the i-bank, I felt part of a well-oiled machine that wasn’t innovating in any direct sense; every day I was perpetuating the behavior of the beast. We can argue that by lending and raising capital, i-banks enable other entities to innovate and improve the status quo, but again, the day-to-day work of an analyst was too far removed for my taste.

I’ll close this discussion on the topic of pay. As I mentioned in my first blog post, coming from an i-bank gives you leverage to use in a negotiation with a start-up. I certainly didn’t come over to the start-up on financial terms that were unfavorable. That said, I left the i-bank just having made associate so I am definitely making less now than I would have been. However, compensation in a start-up is often in equity. While deferred compensation, it might be a whole better to have that in three years from now, when the company sells, than to have a 10k salary increase now.

As you can see, it’s a compromise on each of the points above. You give something up to get something in return. Whether what you get in return works for you is a matter of values.


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