
Student Cases
Investment Banking (Finance)
Investment Banking (Finance)
Campus Sweethearts to Wall‑Street: My Distressed‑Debt & Fixed‑Income Recruiting Journey
Henry grew up in Shenzhen and Jiangsu, finished high school in Florida, and studied at New York University. Drawn to negotiation, contract terms and distressed‑debt restructuring, he shifted to bond‑market structuring after multiple recruiting setbacks. Supported by his girlfriend Susie — an OSG student with an investment‑banking offer — plus OSG coaching, he landed a Wall‑Street role.
Published on
September 24, 2026
16
min read

Unique Personality: Discover My Own Strengths
When I was little and my parents told me to finish homework, I would not jump straight into it. Instead I would say, “Let me play for ten more minutes, then I will start my homework.”
I would add one more condition: “If I go over by one minute, I will read for an extra half‑hour tonight.”
I never saw this as throwing a tantrum. To me, I was setting ground rules: give me room, and I will deliver results.

This trait stayed with me as I grew older and even showed up when I bargained. The first time I travelled to Europe, I spotted a stone souvenir priced at 400 euros on a street stall. The shopkeeper noticed how intently I stared at it and told me flatly: “This price is as solid as the stone itself. No bargaining.”
I shifted my approach. First I talked about the symbolic meaning of the stone, shared my experience visiting this city for the very first time, and explained how genuinely I liked the piece while also being limited by my budget. We chatted for nearly twenty minutes. Finally he relented and cut the price by 170 euros.
What excited me was not saving money. I realized I was good at laying out ideas clearly, figuring out the other party’s bottom‑line expectations, and gradually steering conversations toward closure. I started wondering: is there a job that does exactly this every single day — except instead of haggling over prices, you negotiate hard‑edged rules and contractual clauses?
Forged by Life Challenges: Building Independent Character
My upbringing was far from smooth‑sailing. I grew up in Shenzhen and moved to Jiangsu in fifth grade. I followed the standard local education track through elementary and middle school.
In eighth grade, my mother took me travelling around Europe. That trip opened my eyes to how diverse and dynamic the outside world could be. After returning home, I told my family I wanted to study abroad and began preparing for language exams.
Back then my English foundation was extremely weak; I could not even score 60 on the TOEFL. But I am a stubborn person. To prepare for standardized tests, I moved alone to another city and lived in a hotel for six full months, devoting nearly all my energy to TOEFL and SAT study.
From that experience I learned an important truth: life does not follow some pre‑written path. Every possibility depends on whether you can make clear‑headed judgments and accept the consequences of each choice you make.

Later I moved to Florida for high‑school. I quickly built my own support system and slowly earned trust within a completely unfamiliar environment. That period felt like intentional self‑shaping: learning how to keep moving forward amid uncertainty.
It was also during high‑school that finance became tangible for me. Many of my classmates came from well‑off households. Some parents would even place real capital under student management at school. That was my first time seeing actual money handed over for students to manage hands‑on. I understood finance could be something you actively practice, not just read about in textbooks.
During the summer before my senior year of high‑school, while most peers enjoyed graduation trips, I joined OSG out of curiosity about finance. My mentors guided me to start career planning ahead of schedule.
After I enrolled at New York University, the finance atmosphere felt overwhelmingly intense. Everyone around me talked non‑stop about investment banking and internships, and I got swept up in that current.
I took multiple classes covering mergers & acquisitions and IPOs. Those terms sounded glamorous, yet something kept bothering me. Rather than being fascinated by shiny high‑profile deals, I wanted to dig deeper: which party really benefits from a single sentence buried in a contract? Which exact clause caused an entire transaction to stall?
My mentor Paul pointed me toward distressed‑debt restructuring. Under his guidance, I picked one recent real‑world case every week. I mapped out every stakeholder, clarified each party’s goals, and pinpointed one critical contractual term, summarizing its impact in one clear sentence. After working through more than a dozen cases, my understanding solidified. What attracted me was not simply “winning”, but reshaping outcomes through thoughtful contractual design.
My mentor also broke down club admission preferences and how they matched my background, and built a differentiated application strategy for me.
Instead of competing for over‑subscribed popular student organizations, I followed his precise advice and joined a professor‑led special‑situation investment group. Looking back, the title itself mattered far less than the guided process of clarifying direction and focusing my energy.
The club brought huge value. Professors regularly invited senior leaders from top buy‑side firms including Blackstone and Apollo Global Management to give guest talks. We were not passive audience members; we spoke face‑to‑face with real‑world decision‑makers and unpacked their reasoning.
Most importantly, my mindset shifted. I truly grasped how capital games play out when legal covenants, debt seniority, and control fights all collide. That structural tension fascinated me deeply.
Harsh Realities: Adjusting My Recruiting Direction
The reality was tough: there are extremely few restructuring‑focused roles available. Paul had warned me long before that fewer than one hundred such positions open industry‑wide each year.
At that time I was too single‑minded. I fixated only on restructuring and barely considered other options. Rejection after rejection from interviews left me stuck in mental exhaustion and confusion.
I talked through this struggle over and over with my girlfriend Susie, who is also an OSG participant. She had already landed an investment‑banking offer and kept an extremely busy schedule herself. Even so, she set aside one hour every night to listen to recordings from my mock interviews and mark key observations for me. Honestly, without her support, my anxiety would have worn me down completely.
Through repeated conversations, I finally pulled the core question out from under all my emotional stress: should I keep chasing this long‑shot niche track, or step back and pursue adjacent work where I could apply similar skill sets?

After reviewing my situation, Paul guided me to list out all my core priorities one by one. We realized bond‑market work would be a strong fit. It also involves structuring work, requires deep understanding of both investor and issuer mindsets, and demands constant awareness of market windows and pricing within fast‑paced workflows.
Once my target direction was set, a new practical challenge appeared. Technical knowledge could be built within two weeks of concentrated, systematic training. The harder part lay in behavioral interviews: how to make every answer feed into one consistent personal narrative, instead of assembling ten disconnected versions of myself.
If you only practice alone, you can easily fall into the illusion that your answers sound solid. You will not notice when you speak too fast, jump between topics, or stay overly abstract. No one will give you real‑time feedback, and you may fail to spot those gaps in self‑review afterwards.
This is one major advantage of working with OSG. In every mock‑interview session, mentors pointed out my blind spots directly and helped me improve. One piece of feedback from Paul stuck firmly in my memory: “All your answers are fine, but after listening to you, I still cannot tell who you really are.”
I realized behavioral interviews are not just about getting every answer technically correct. Every response should tie back to one unified personal story. Paul spent substantial time with me polishing this consistent narrative thread.
I stopped making generic claims such as “I am good at communication”. I no longer shied away from past missteps. Instead I clearly explained how I adjusted and recalibrated my approach after setbacks. In the end, every experience and choice needs to answer one underlying question: who am I?
Good Fortune Arrives: Every Step Has Been Worthwhile
My final‑round interview arrived before February. I performed well that day. Interviewers asked granular follow‑up questions, not to grill me, but to push me to walk through my full logic step‑by‑step.
Less than one hour after the interview wrapped, a vice‑president sent an email. He wanted to set up a coffee chat to introduce me to a colleague working on asset‑restructuring work. I paused and wondered: what kind of new interview format was this?

When our 9 a.m. meeting started the next morning, I understood. This was no casual coffee chat — it was an additional testing round. He jumped straight into technical questions without small talk. My heart raced, yet I was grateful for my thorough preparation; I did not get thrown off‑balance by the high‑pressure setting.
Nearly every question he raised was something I had already challenged myself with while dissecting past cases. When you truly understand how contractual rules operate, interviewers can tell instantly.
Half‑way through our talk, he visibly relaxed. He started sharing stories about difficult‑to‑please clients from their real‑world deals and practical on‑the‑job transaction details. Right after our Zoom call ended, a new email popped into my inbox. Before I could wonder whether a third round was coming, my phone started ringing.
Seeing a New‑York‑area number, I pulled a friend over to take the call together. The person on the line opened with “congratulations”. I kept repeating “thank you”, while one thought looped in my head: I actually made it.
I had collected so many rejections throughout recruiting. Many interviews ended without feedback, leaving me guessing what went wrong. After I hung up that offer call, I sat quietly in my room and re‑ran my whole journey through my mind. Every single step had mattered.
Immediately after the call I messaged Susie. She sent back a simple smiling emoji: “I knew you could do it.” There were no dramatic exclamations or long paragraphs. It was as if she had never once doubted this outcome.
At that moment it hit me: half the weight of this win belonged to her. When rejections numbed you and self‑doubt crept in, there is immense value in having someone who sees your potential and believes in you more firmly than you believe in yourself.

Recruiting taught me one profound lesson: being talented does not guarantee you will get noticed. You have to persist through long stretches where you receive zero feedback at all.
That boy who once negotiated ground‑rules with his parents and patiently bargained with shopkeepers abroad finally found a role where his genuine interests become day‑to‑day real‑world work.
*Disclaimer: OSG has no cooperation/affiliation with the companies mentioned in the article; OSG students enhance their abilities through OSG services and secure offers through regular campus recruitment/social recruitment channels.
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Book Your Free Session →Frequently Asked Questions
Goldman Sachs investment‑banking interviews evaluate technical mastery, deal awareness, logical communication, and genuine fit with team culture. Beyond textbook accounting and valuation knowledge, interviewers pay close attention to how candidates connect personal background to banking work, and observe how you think through open‑ended real‑world deal scenarios.
JPMorgan summer‑analyst recruiting generally opens far earlier, often launching during sophomore year. Full‑time recruiting accepts candidates who missed summer‑internship windows. Even for full‑time roles, applicants still face strict technical and behavioral evaluation; prior relevant internship experience remains a strong plus but is not an absolute hard requirement.
Both firms value solid technical foundations, yet they weight prior niche‑track exposure differently. Goldman Sachs tends to look for deep case‑study familiarity for restructuring‑focused applicants. JPMorgan places relatively more emphasis on transferable analytical skills and market‑sense potential, and will train promising candidates who do not come with fully‑built niche‑industry background.







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