I wore a LOT of J. Crew in high school and college. I didn’t know it then, but my love for J. Crew would eventually spark my interest in private equity (PE).

In March 2011, when I was a high school sophomore buried in SAT prep, J. Crew was acquired by TPG Capital and Leonard Green. Fast forward five years to my junior year of college when I walked into J. Crew and felt so underwhelmed by the lackluster designs – so much so that I pulled out my phone and googled “What is going on with J. Crew?” and “Did J. Crew change their creative director?”

That Google search sent me down a rabbit hole – and eventually into the world of private equity. Although I wasn’t thrilled about the demise of my favorite clothing brand, I became fascinated by leveraged buyouts (LBO), especially the aspects of financial engineering and value creation. That day, I made a decision: I was going to become a private equity investor.

Nearly ten years after that fateful store visit, I’ve built almost four years of private equity experience across both large-cap and middle-market LBOs. I wanted to share a few reflections on what I’ve learned and how my thinking has evolved.

As previously mentioned, I moved from NYC to LA in April 2021 to join a large-cap, traditional LBO PE firm investing out of its $10bn flagship fund. After 2.5 years there, I was recruited to join a new PE firm that spun out from my first PE firm, where I focused more on middle market LBOs and complex carveout transactions.

My private equity experience was truly invaluable. It sharpened both my technical M&A execution abilities and my soft skills in so many ways.

Key Technical Takeaways

1. 360° View of M&A: In investment banking (IB), I executed M&A transactions to sell companies. In private equity, I executed deals to buy companies. That dual perspective gave me a full picture of how deals actually come together. As an IB analyst, I created marketing materials to send to PE firms. In PE, I learned what actually happens behind the scenes in reviewing and analyzing those documents – how PE firms think through valuation, risks, transaction structure, and build conviction internally. On my first PE deal, I was amazed at how much thought and work go into preparing a single LOI package.
2. The Art of Corporate Finance: As the saying goes, valuation is more art than science. My IB analyst years taught me the mechanics of valuation, but PE taught me how to think through a framework of risk vs. reward, cost vs. benefit, sources vs. uses, and how those shape valuation. It’s not just about numbers – it’s about judgment.
3. Due Diligence: I learned to sift through large volumes of information to identify what is and isn’t important – and why. It’s not just about knowing where to find the data, but also how to use that data in your analyses and what conclusion it supports. Being resourceful is also crucial: when the data needed doesn’t exist, what else can you use to triangulate the answer? Another key skill I learned was managing all the various diligence advisors to get your transaction workstreams going and also knowing when and how to push them for insights so they are not regurgitating information from the sell side advisors.
4. Value Creation & Portfolio Management: Private equity “value creation” always seemed like a black box to me, so it was eye-opening to see how the work actually unfolds post-acquisition. I worked very closely with the management teams of my portfolio companies on various strategic initiatives – add-on acquisitions, monetization deals, financings, entering into adjacent markets, and so on. These experiences helped contextualize how the quality of a management team directly impacts outcomes. There is a real difference between an outstanding management team, a good one, and a bad one. What may look like a great plan on paper doesn’t go far without the right people executing it.
5. The Business Side of Private Equity: Beyond deal execution, I found it equally fascinating to see how a private equity firm itself operates. At my second PE firm, I got a close-up view of how a PE firm is built – how PE fundraising works, how to pitch your investment strategy to LPs, how return metrics are calculated and presented to fund investors, and the critical role that different LP institutions play in the broader PE ecosystem. It was a valuable reminder that while we’re investing in companies, we are also managing one. The infrastructure of Wall Street never fails to amaze me – it is so interconnected and well-built that it makes so many products, like an LBO, possible.

Soft Skills I Developed

1. Operating Under Ambiguity: Most of my assignments were open ended with minimal direction. This was intimidating at first, but over time, I gained confidence in navigating ambiguity and even began to enjoy the autonomy. I learned to become comfortable running my own analyses and saw it as an opportunity to show the partners my thought process. Requests from the partners often looked like the following:
   • “This investment banker recommended I check out this company. Can you take a look and let me know what you think?”
   • “Please prepare an investment committee (IC) memo by next week.”
   • “Our portfolio company CEO wants to acquire this business. Can you assess if it makes sense?”
   • “An LP asked if we’re considering investing in XYZ industry that we know nothing about. We want to get back to them with a thoughtful answer, so tell us what we need to know about the space and what you think about it.”
2. Forming an Opinion: This was the biggest contrast for me coming from banking. As an IB analyst, I mostly executed what the managing director wanted to show. In PE, it was on me to dig into the data and form my own opinion. At first, this was intimidating since I was often the first person to review any investment opportunity that came across our desks. Over time, I became comfortable once I realized that in investing, there’s no “right” answer – the key is to communicate your findings and rationale clearly. It’s perfectly okay if someone else thinks differently. In fact, differing opinions spark discussions that often uncover new perspectives neither side had considered.
3. Accountability: Since I was closest to the numbers and data, it was my responsibility to catch anything critical – missing something could have massive consequences, including the potential to lose hundreds of millions of dollars. One of the first things I was told on the job was “Always work like your ass is on the line” – it sounds intense but it is actually great advice for any high stakes job.
4. Communicating Your Opinion: Throughout my time in PE, I wrote more than 300 pages of investment write-ups, not including IC memos. Looking back, I think I truly received excellent training in writing from my first PE firm. Conducting due diligence is one thing, but being able to clearly and concisely communicate your findings to your various constituents is another. Who is your audience (key IC members, lenders, lawyers and advisors, LPs) and how are you going to tailor your messaging accordingly? What is must know vs. good to know? If the partner called you one minute before an important meeting, what are the top three points you need to say? Learning how to distill complex findings and tailor them to different stakeholders was one of the most useful and transferable skills I took away from PE.
5. Humility, Patience, and Trust: In the M&A industry, people often say that deal reps are everything, and I wholeheartedly agree. No two deals are the same. Just when you think you’ve seen it all, a new transaction presents a unique nuance. It takes time and patience to build those reps. Just as important is learning to balance confidence and humility: when someone disagrees with your opinion or conclusion, don’t get defensive – instead, listen and learn because their perspective might reveal something you missed. With each transaction, you sharpen your judgment: learning where to dig deeper, which assumptions to pressure-test, and which signals to trust.

Looking back on my career thus far – from my J. Crew obsession to M&A consulting, investment banking, and eventually private equity – it’s been a wild ride. Private equity is a notoriously exclusive industry infamous for grueling recruiting cycles (which I can definitely attest to), so I feel incredibly fortunate to have had the opportunity to work in the space with very intelligent people at established firms.

Private equity was a demanding job, but it consistently kept me intellectually stimulated. Private equity challenged me, stretched me, and taught me how to think more critically, strategically, and independently. Everything I’ve learned over the past four years will be invaluable as I turn the page to the next chapter of my career… Stay tuned.

Thank you for reading,
Phyllis