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👋🏻 A Note from the Writers
Hey guys, it’s Hasan and Austin! We’re students at the University of Toronto and write the PrepStreet newsletter (Mondays and Fridays at 12pm).
We’re trying to make some resources to give away, any ideas? Request anything here - makes our life super easy because we’ll know exactly what you want. Be it resumes, coffee chat guides, interview questions, or something else. We’ll create a list and start working on it :)
doing anything under the sun to one-up you…
💼 Recruiting Radar
Relevant Job Postings:
Barclays Fall 2026 New Grad Analyst
Application Deadline: Rolling
Location: Toronto, Ontario
Connor Clark & Lunn Fall 2025 Trade Execution Analyst
Application Deadline: Rolling
Location: Vancouver, British Columbia
Global Millennial Capital Fall 2025 Investment Analyst
Application Deadline: Rolling
Location: Boston, Massachusetts
Application Deadline: Rolling
Location: New York, New York
Stay tuned for our upcoming job posting tracker…
📈 This Week on the Street
What is a recent story you’ve been following in the markets?
Credit and Cuts:
I’ve been following is how markets are behaving like two different animals at once, the credit market is acting nervous even as a handful of huge tech names are powering equities higher. Practically speaking, corporate credit looks extremely tight, investment-grade spreads are around their lowest levels in decades and some measures sit right near 1998 lows. This tells me investors are pricing in a very rosy growth scenario. At the same time, the latest jobs revisions cut several hundred thousand positions from prior months and that shock pushed traders to reprice rate-cut odds aggressively, creating violent moves in treasuries.
On the other hand, equities are being driven by a very narrow group of megacaps, the top 10 names now make up roughly 37% of the S&P by weight, so headline index strength is masking a lot of dispersion underneath. My read is: those credit signals are a leading indicator, they often warn before equities do, so I’d be careful with credit beta and crowded high-yield exposure, while still owning select, high-quality large caps that have strong earnings and buyback support. That means hedging credit risk (or favoring higher-grade) and looking for opportunities in the improving breadth once we see clearer macro data.
💸Deal Dive
What’s a Recent Transaction You’ve Been Following?
Interview Script:
Sycamore Partners (advised by UBS) to acquire Walgreens Boots Alliance (advised by Centerview Partners) Merger - Announced March 2025
Company Descriptions
Walgreens Boots Alliance (WBA) is one of the world's largest retail pharmacy, health, and wellness companies. WBA operates more than 12,500 stores globally and employs roughly 312,000 people. Core businesses include prescription fulfillment, health and wellness services, and a broad portfolio of retail pharmacy brands.
Sycamore Partners is a New York-based private equity firm specializing in investments, turnarounds, and value creation within retail and consumer sectors.
Buyer’s Rationale
Scaled and Diversified Portfolio: The merger creates a combined enterprise with a robust, diversified branded pharmaceuticals portfolio and a scaled generics business. Key brands now include Acthar® Gel, INOmax®, Terlivaz®, and XIAFLEX®, along with an extensive roster of over 80 generic products and 40 sterile injectables.
Financial and Strategic Flexibility: Combining entities increases strategic and operational flexibility, expands business development potential, and establishes a strong foundation for future growth in higher-margin branded drugs.
Synergy Realization: Projected to generate more than $150 million of annual pre-tax run-rate operating synergies by year three; $75 million expected within the first year, derived from streamlined manufacturing, R&D consolidation, and shared services.
Post-Restructuring Strength: The new entity emerges with an improved balance sheet, approximately $2.8 billion in net debt (2.3x 2025E pro forma adjusted EBITDA), and the benefit of legal clean-slate status, enabling renewed focus on growth investment.
Seller’s Rationale
Immediate and Potential Value for Shareholders: WBA shareholders receive $11.45 per share in cash at closing, plus non-transferable Divested Asset Proceed Rights (“DAP Rights”) to receive up to an additional $3.00 per share from the future monetization of WBA’s interest in VillageMD and related assets. This represents a total potential consideration of up to $14.45 per share - an up to 63% premium to the closing price.
Participation in Turnaround Value Creation: The DAP Rights enable shareholders to participate in future asset monetization and value creation driven by Sycamore’s restructuring and operational plans.
Go-Shop Flexibility: WBA’s process included a 35-day “go-shop” period to seek superior proposals, maximizing competitive tension and assuring shareholders of a robust process.
Key Stats
Deal Size: Up to $23.7 billion (enterprise value)
Per Share Offer: $11.45 cash plus up to $3.00 per share via DAP Rights, for total potential consideration of $14.45 per share
Premium: Up to 63% above undisturbed price; 29% premium for cash portion
DAP Rights Structure: Each WBA shareholder will receive one DAP Right per share at closing, representing 70% of the net proceeds from the sale of VillageMD and related assets, capped at $3.00 per share (about $2.7 billion total for DAP Rights holders)
Divested Assets Financial Trajectory: Divested assets (VillageMD, Summit Health, CityMD) projected to improve adjusted EBITDA by $292M YoY in 2024, with continued margin expansion over next five years; sale processes for certain markets underway in 2025
Opinion
This buyout underscores the strategic imperative for retail and healthcare companies to pursue deep operational and financial restructuring once public market pressures become unsustainable. Sycamore’s private ownership model and turnaround expertise are likely to accelerate operational changes, cost rationalization, and core segment investment.
The innovative DAP Rights structure aligns current shareholders with future value creation, offering both liquidity and upside from asset monetization.
Regulatory approvals, debt leverage (83% financed by debt), and real operational transformation present significant risks, but also potential for meaningful long-term value enhancement and repositioning of one of the world’s largest pharmacy chains.
Sources: Investor Relations Deck, Press Release
Big investors are buying this “unlisted” stock
When the founder who sold his last company to Zillow for $120M starts a new venture, people notice. That’s why the same VCs who backed Uber, Venmo, and eBay also invested in Pacaso.
Disrupting the real estate industry once again, Pacaso’s streamlined platform offers co-ownership of premier properties, revamping the $1.3T vacation home market.
And it works. By handing keys to 2,000+ happy homeowners, Pacaso has already made $110M+ in gross profits in their operating history.
Now, after 41% YoY gross profit growth last year alone, they recently reserved the Nasdaq ticker PCSO.
Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.
🫱🏼🫲🏼 Interview Lab
Technical Questions (answers below!):
EASY: What type of companies could have a negative Enterprise Value?
MEDIUM: When would you use the Gordon Growth method instead of the Terminal Multiple method in a DCF?
HARD: You have an asset with a gross value of $1000 and a net book value of $400. You sell the asset for $600 in cash. Assume a 40% tax rate. Walk through the 3 statements.
Technical Answers:
A:
Financial institutions with large cash balances
Distressed companies where debt exceeds equity value
Tech companies with large accumulated losses and significant cash holdings
A:
The business is cyclical and multiples may vary too much over time
The company is too large for realistic acquisition multiples (e.g., Apple)
There’s no good set of comparable companies to benchmark against
A:
Income Statement:
Gain on sale = $600 – $400 = $200
Pre-tax income = +$200
Taxes = –$80
Net income = +$120
Cash Flow Statement
Net income = +$120
Subtract gain on sale (non-cash) = –$200
Cash from investing = +$600 (sale proceeds)
Net cash flow = +$520
Balance Sheet
Cash = +$520
PP&E = –$400 (remove NBV of asset)
Retained earnings = +$120
Behavioural:
Q: How would you describe your leadership style?
Advice:
Anchor in a specific story: A real example grounds your leadership style in lived experience rather than abstract traits.
Balance drive with humility: Show that you know when to lead from the front and when to step back and leverage others’ strengths.
Highlight growth: Incorporate a learning arc - what the situation taught you about leadership and how it’s shaped your approach since.
Sample Answer (this is Hasan’s):
I’d describe my leadership style as being able to step up and drive when needed, but also knowing when to take a step back and create space for others to contribute at their highest level. When I was interning at Bank of America, I was staffed on a pitch to a SaaS company where I had to build an LBO acquisition financing model and create case toggles for various scenarios. I had never done a model before on the job, and I was given less than 24 hours to turn it around. My Analyst told me I’d be driving the work end-to-end before presenting it to the Associate.
It’s easy in high-pressure situations to think you need to figure everything out yourself, but I knew the fastest way forward was to combine my skillset with the team’s experience. Before even opening Excel, I asked my Analyst if there were any templates or past models I could reference and how he’d think about structuring this. That 30-minute sync gave me the clarity to work efficiently.
From there, I worked in fast iteration cycles, checking in every 2–3 hours when I had meaningful progress. These short feedback loops helped clear assumptions early and ensured my rationale was sound. I think that’s the essence of good leadership - keeping momentum high, ensuring alignment, and making sure every person is contributing where they have the most impact.
By the end, the Associate told me my work was at a full-time Analyst (II) level, and I got to present it to the Director. It was validating, but more importantly, it reinforced that leadership is about balancing decisiveness with humility.
Important Takeaways:
Demonstrates Leadership Under Pressure: Shows the ability to take ownership in a high-stakes, time-constrained environment while still maintaining composure.
Highlights Humility and Collaboration: Emphasizes leveraging others’ expertise, not just relying on individual effort—avoiding the “I did it all myself” trap.
Shows a Clear Learning Arc: Moves from being caught off guard to delivering senior-level work, tying it back to a core leadership philosophy that’s memorable and applicable.
A quick recruiting tip: If you don’t follow up within 5–7 days of no response, you’re losing 30–40% of potential replies. People are busy, not uninterested, half the battle is just reappearing in their inbox. Send those follow ups!
See you Friday!
Prep St. Insider Team