Day in the Life of an Investment Banker: Three Real Days

Phone buzzes on the nightstand. Email from my associate Maren. Subject line: "CIM comments." The CIM is the confidential information memorandum, basically the sales document for the company we're marketing. We sent a draft to the client's CEO yesterday for review. He came back with 23 comments overnight. Twenty-three. On a document we'd already revised four times. I open the email and skim the comments while still in bed. Most of them are phrasing things. He wants "innovative" changed to "differentiated." He wants the revenue chart to show quarterly instead of annual. One comment says "this doesn't feel right" with no further explanation. That one will take me 45 minutes to decode.

At the office. Kips Bay to Midtown, 7 train to shuttle. Floor 38. I sit in an open plan area with about 15 other analysts. My desk has two monitors, a keyboard, a company-issued laptop, and a half-empty bottle of Advil. The analyst next to me, Priti, is already deep into something. Headphones in. She's on a different deal. We don't talk much during the day. The work doesn't allow it.

Start working through the 23 comments. The "innovative" to "differentiated" swap is easy. Find and replace. Done in two minutes. The quarterly revenue chart requires me to go back into the model, pull the quarterly data, build a new chart in Excel, format it to match the firm's style guide, paste it into PowerPoint, resize it, align the axis labels. That takes 40 minutes. The "this doesn't feel right" comment is on the market overview slide. I email Maren: "Do you have context on comment #17? He says 'doesn't feel right' but doesn't specify." Maren responds 20 minutes later: "I think he wants more emphasis on the premium positioning. Call me if stuck."

Fifteen of the 23 comments are done. The remaining eight require judgment calls. Maren and I do a 20-minute call where we go through each one. She makes decisions on six of them in real time. Two she escalates to our VP, Lucinda, who is on a plane to Minneapolis for a different client meeting and will respond when she lands. I continue revising while waiting.

Lunch. A turkey avocado wrap from the lobby deli. $14.50. I eat it at my desk while formatting the appendix section of the CIM. The appendix is 28 pages of financial exhibits: historical income statement, balance sheet, cash flow, customer metrics, cohort analysis. Each table has to match the rest of the document. Calibri 9. Navy headers. Gridlines in #D9D9D9. I know the hex code by heart. That feels like a thing I should be concerned about but am not.

Lucinda responds from Minneapolis. She's approved six of the remaining comments and pushed back on two. She wants me to keep the annual revenue chart alongside the quarterly one, not replace it. So now I need to fit two charts on a page that was designed for one. I spend 45 minutes on layout. The page looks crowded. I call Maren. She says to move the market size data to the next page and use the freed space. I move it. The page numbering shifts. Three cross-references in the executive summary now point to the wrong pages. I fix the cross-references. This is the job.

All 23 comments are addressed. I send the revised CIM to Maren for review. She'll go through it, mark it up, send it back. That cycle usually takes an hour. In the meantime, I pull up a separate project: a buyer list for a different deal that Lucinda staffed me on yesterday. I need to identify 30 potential acquirers for a specialty food brand. I open Capital IQ, search for companies in the specialty food and natural products space, filter by revenue ($50M to $500M), and start building the list in Excel. Name, revenue, EBITDA, ownership (public, PE-backed, family-owned), headquarters, relevant acquisitions. Each company takes about 8 to 10 minutes to research. I get through 12 before Maren's markup comes back.

Maren has seven comments on my revision. Three are formatting issues I missed. Two are substantive. She wants me to add a footnote explaining the quarterly revenue seasonality. She also flagged a cell in the financial exhibit where the EBITDA margin rounds to 22.4% in the table but 22.3% in the chart because the chart is pulling from a different cell. I trace the discrepancy. The chart pulls from the detailed model (which uses more decimal places) and the table pulls from a rounded summary. Both are technically correct but they can't show different numbers. I update the chart to pull from the same rounded summary. The difference is one-tenth of a percentage point and nobody would have noticed, but if they did notice, the credibility of the entire document would be questioned. I fix it. Fifteen minutes.

Final CIM sent to the client for overnight review. If he approves, we'll send it to the buyer list tomorrow. If he has more comments, we do this again. My phone says the Seamless guy is 8 minutes away. Chicken tikka masala. Order #68.

Back to the buyer list. Get through companies 13 through 25. One of them, a PE-backed platform in Portland, acquired three specialty brands in the last two years. I flag it as a high-priority target and add notes on their acquisition strategy. Lucinda will want to know this. I add a "key takeaway" column to the Excel sheet because I know she'll ask for it and I'd rather do it now than redo the entire list tomorrow.

Buyer list is at 25 of 30. Close enough for tonight. Save. Email to Lucinda with "WIP buyer list, 25/30 complete, will finish AM." Pack up. Walk home. Murray Hill is quiet. My roommate Theo is on the couch watching basketball. He's a medical device sales rep. He was home by 6. He asks how my day was. I say "comments." He nods. He's learned that "comments" is a self-contained explanation. I eat a yogurt, look at the buyer list on my phone for no reason, put the phone face-down, and go to sleep.

Up before the alarm. Lie in bed for four minutes checking email. Nothing from the sell-side client, which is good. An email from the buy-side client's CEO, Dr. Okafor, timestamped 11:47 PM: "Want to revisit the synergy assumptions before Friday's board call. Can we connect today?" I reply immediately: "Of course. How's 2 PM?" I know his schedule. He has clinic in the morning. He replied while I was typing: "2:30 works." So that's now the anchor of my afternoon.

At the office. Our floor is half-empty because the industrials group is on a deal trip. The quiet is nice. I open the buyer list for the home health deal. We've received IOIs (indications of interest) from seven buyers. The deadline was Monday. I need to compile them into a summary for my MD, Tobias, by noon. Each IOI has a proposed value range, deal structure preferences, financing details, and due diligence requests. I open a template and start entering the data. Buyer A: $88M to $95M enterprise value, all cash, 60-day exclusivity. Buyer B: $82M to $90M, cash with a $5M earnout tied to 2027 revenue. Each one takes about 15 minutes to summarize properly.

Internal deal team call for the home health process. Tobias, me, Deshawn, and Kendra (our associate). Tobias wants to narrow the seven IOIs down to three for management presentations. He asks me who I'd cut. I recommend keeping Buyers A, C, and F. A has the highest valuation. C is the most credible strategic acquirer. F is a PE firm with a strong track record in home health and their earnout structure could get the seller to $98M if they hit the targets. Tobias agrees on A and C, pushes back on F. He thinks the earnout structure is too complex for our client, who is a 62-year-old founder who wants clean and simple. He substitutes Buyer D, which is a strategic with a lower headline number ($85M) but all cash, no contingencies. I make a note. Tobias is probably right. Our client, Marlene, has said three times that she wants "a clean deal." When a seller says something three times, you listen.

Finish the IOI summary with the three finalists highlighted. Send to Tobias. He responds in 12 minutes: "Good. Set up a call with Marlene tomorrow." I email Marlene's assistant to schedule. Then I switch to the buy-side deal.

The buy-side deal is more complicated. Dr. Okafor's behavioral health platform wants to acquire a competitor, a company doing about $40M in revenue with 12 clinics across three states. The acquisition would make his company the largest outpatient behavioral health provider in the Southeast. We're in diligence. The target's financials are in a virtual data room. I spend an hour in the data room reviewing the target's payor mix. Commercial insurance is 61%, Medicaid is 28%, self-pay is 11%. The Medicaid concentration concerns me. Reimbursement rates are set by the state and they don't keep up with cost inflation. If the states cut Medicaid rates by even 3%, it would knock $340,000 off annual revenue. I make a note for the synergy model.

Lunch with Kendra at a Thai place two blocks from the office. She's been on the team for eight months and she's good. Sharp on models, still learning the client management piece. She asks me how I handle it when Tobias and I disagree on deal strategy. I tell her the truth: Tobias has closed 45 deals. I've closed 9. When we disagree, I say my piece clearly, and if he still disagrees, I defer. The one exception is accuracy. If the numbers are wrong, I don't defer. Numbers are not a matter of opinion. She nods and writes something in her notebook. I notice she writes with a Pilot G-2 07 in blue. I don't mention it.

Call with Dr. Okafor. He wants to understand the synergy assumptions in our model. Specifically, he's concerned that we're projecting $3.8M in cost synergies from consolidating back-office functions, and he thinks the real number is closer to $2.5M because "you can't cut the billing team by 40% without losing claims." He's a practicing psychiatrist who also runs a $45M company. When he pushes back on a financial assumption, it's grounded in operational reality. I tell him I'll rework the synergy model with a more conservative staffing assumption and send him a revised range by Friday morning. The call is 38 minutes. When we hang up, I feel like I learned something about behavioral health billing that will make the model better. That happens about once a week, where a client's pushback improves the analysis. I try to notice when it does.

Sit down with Deshawn to rework the synergy model. Walk him through Dr. Okafor's feedback on the billing team assumption. Deshawn asks good questions. He wants to know why we can't just ask the target's CFO for the actual back-office headcount instead of estimating it. I tell him we can, but the target doesn't know we're questioning the synergy number, and tipping our hand about where we think the savings are could affect the negotiation. He says "that's political" and I say "that's deal work." He adjusts the model. We land on a revised synergy range of $2.4M to $3.2M.

Tobias stops by my desk. He wants to talk about a new pitch he's scheduled for next week. A physician staffing company in Nashville that might be considering a sale. He wants me to build a preliminary deck, 15 pages. Industry overview, comparable transactions, preliminary valuation range. I tell him I can have it by Monday. He says Tuesday is fine. I make a note and add it to the Mondrian calendar. Tuesday is now red.

Leave the office. This is early for a banker and I feel the instinct to justify it, which is absurd. Nobody is tracking my departure time. The middle-market hours are better than the bulge bracket. I worked until 1 AM maybe four times in the last year. Most nights I'm home by 8. The trade-off is that I'm on-call always. Tobias can text me at 10 PM and I'll answer. Dr. Okafor emailed at midnight. The hours are bounded but the availability is not.

Home. My partner Zola made roast chicken. She's a landscape architect. We eat at the table, which is non-negotiable. Phones face-down. She tells me about a park redesign project in Decatur that's behind schedule because the city council can't agree on whether to keep a particular oak tree. I tell her about Tobias substituting Buyer D for Buyer F. She says "trust the old guy." She's right. She usually is about the people stuff. After dinner I open my laptop for 30 minutes and review the revised synergy model that Deshawn sent. It looks good. One formula is pulling from the wrong tab. I flag it in a comment and close the laptop. Not tonight.

Alarm. I have a 7:30 AM flight to San Jose. Client meeting at noon. Pack was done last night. Navy suit, backup shirt, charger, the leather portfolio that Carmen gave me when we started the firm. I make coffee in the kitchen while Noa is getting ready for school. She asks if I'll be at her debate tournament Friday. I tell her I'll try. She says "that means no" and goes upstairs. She's 14 and she has figured out my vocabulary. "I'll try" means probably not. "Absolutely" means yes. I have not said "absolutely" to a school event in about six weeks.

Uber to DEN. Airport is 35 minutes from our house in Wash Park. I use the drive to read a board presentation that a client sent me last night. He's the CEO of a managed services company, about $65M in revenue. His board wants an update on strategic alternatives, which is code for "should we sell." He asked me to sit in on the board call next Tuesday as an outside advisor. I'm reading the deck to understand the board dynamics. Three of the five board members are PE partners. They want liquidity. The CEO, Garrett, wants to keep running the company. The tension is the entire engagement.

Board the flight. United, first class, because the firm pays for first class on anything over two hours and because I will absolutely lose my mind in a middle seat at this point in my career. Open my laptop before they close the overhead bins. Start reviewing the pitch materials that my team prepared for the noon meeting. Suki, my VP, put together a 25-page deck on the potential sale of a SaaS company in San Jose. The founder wants to explore. We're pitching to be his advisor. The deck looks good. One thing bugs me: the comparable transactions section includes a deal from 2023 that traded at 12x ARR. That was a different market. Including it sets an unrealistic expectation. I text Suki: "Remove the 2023 outlier on page 14. The founder will anchor on it and we'll spend the entire relationship managing that expectation down." She replies before takeoff: "Done. Updated PDF attached." Good.

Land in San Jose. Uber to the founder's office, which is in a converted warehouse in North San Jose. The company does contract lifecycle management software. About 200 employees. The founder, Kit, built it from nothing over seven years. He's 41 and he's at the point where the PE board that invested in his Series B is pushing for an exit, and Kit doesn't know if he wants to sell or raise another round and keep going.

The pitch meeting. Kit, his CFO Reshma, and their corporate counsel. Me and Suki, who flew in from our San Francisco sub-office this morning. I lead the presentation. Twenty-five slides, but I only show about 12. The rest are appendix. The conversation matters more than the pages. Kit asks good questions. He wants to know what the process looks like and how long it takes. I tell him: four months from engagement to signed LOI, another two to three months to close. Six to seven months total. He winces. Reshma asks about fees. Our advisory fee is 1.5% of enterprise value with a minimum fee of $2.5 million. On a deal this size, probably $275M to $350M in enterprise value, that's $4.1M to $5.25M. Reshma doesn't react. She's seen these numbers before. Kit reacts. He says "that's a lot of money for introductions." I say, "It's not introductions. It's knowing which six buyers will pay the most, knowing which two will move fastest, and knowing how to play them against each other in a way that adds $20 to $40 million to your outcome." Kit looks at Reshma. Reshma shrugs. We'll hear back by Friday.

Lunch with Suki at a ramen place near the office. She asks me how I thought it went. I say 60/40 we get the mandate. Kit is ready but he doesn't know he's ready. The PE board will push him. Reshma is pragmatic and she's already done the math. Suki asks what would move the odds. I say: send Kit a one-page follow-up with three specific buyers I think would be interested and a ballpark timeline. Not the full analysis. Just enough to make the process feel tangible instead of abstract. She makes a note.

Phone call with Garrett about Tuesday's board call. He's nervous. His PE investors want a $200M+ exit. The company's EBITDA is $9M. At the multiples we're seeing in managed services, the realistic range is $110M to $140M. The gap between what the board expects and what the market will bear is my problem to manage. I tell Garrett: "Let me present the market data on Tuesday. Let the numbers make the argument. You don't have to be the one who tells them the number is lower." He exhales. "OK." He pauses. "Everett, is my company worth $200 million?" I pause. "No. It's worth what someone will pay for it, and right now that's probably $120 to $135 million. That's a very good outcome for a company you built from scratch." He says "OK" again but quieter.

Uber to the airport. Flight back to Denver at 6:10 PM. In the car I check email. Seventeen new messages. Three from my co-founder Mitchell about a potential new hire. Two from a lawyer on the home healthcare deal in Texas that's approaching purchase agreement stage. One from Carmen: "Wes got an A on his science project. The volcano worked." I reply with a thumbs up and then feel bad about replying with a thumbs up to a message that deserved more. I type: "Tell him I'm proud and I want to see it when I'm home." Send.

Flight. Three hours. I use the first 90 minutes to review the purchase agreement markups from the Texas deal lawyer. The buyer wants a 24-month non-compete for the seller. The seller wants 12 months. I draft an email to the seller's counsel suggesting 18 months with a carve-out for advisory work. This is negotiation by email at 35,000 feet. The Wi-Fi is $8. I expense it.

Home. Carmen is reading on the couch. Wes is asleep. Noa is in her room. I put my bag down and sit next to Carmen. She says "how was it." I say "good pitch." She says "are you home Thursday?" I check the calendar. "Yes. Thursday and Friday." She says "Noa's debate is Friday at 3:30." I look at the calendar again. I have a call at 2 PM that should end by 3. "Absolutely," I say. Carmen looks at me. She knows my vocabulary too.