I want to be precise about the title. I didn't raise $60M by myself from my desk on the strength of a pitch deck. Fundraising is a team sport and the founder is always the lead. What I did was run the process (build the data room, manage investor relationships, coordinate diligence, structure the narrative) while Retailo raised $60M in a growth round across equity and venture debt. That distinction matters.
I also learned more about capital markets running that raise from the inside than most MBA graduates learn in two years of coursework. The lessons aren't what you'd expect.
B2B commerce, GCC markets, growth-stage. We were operating in Saudi Arabia, Pakistan, and the UAE. The round had both equity and venture debt, which meant managing two completely different investor psychologies simultaneously.
Equity investors buy a story about the future. They're making a probabilistic bet on a large outcome. You influence that bet by making the future feel less uncertain: clean metrics (auditable, consistently defined), a coherent growth thesis (logical, honestly presented), and a team they trust to execute.
Venture debt investors are different. They're underwriting repayment risk. If things go sideways, can this company service the debt? They care about different numbers: revenue quality, customer concentration, churn, cash conversion cycle. Same company. Completely different diligence conversation.
Running both processes simultaneously was one of the hardest things I've done professionally. Not technically. Contextually. You internalize how each investor type thinks and translate the same business reality into their framework, without saying different things about what's actually true.
The data room is where most fundraises are won or lost, and nobody talks about it in founder advice content. Everyone talks about the pitch. The pitch is maybe ten percent. Diligence is ninety percent. Diligence happens in the data room.
A good data room is organized by investor question, not company structure. Investors want to understand the business in a specific sequence: market, model, metrics, team, risks. They don't care that your company organizes into finance, operations, and commercial. Build the room around their mental model, not yours. Every document should answer a specific likely question. Every metric defined, with the definition attached. Nothing should require a follow-up email.
Board dynamics during a raise are their own complexity. I managed a seven-member board during an active fundraise. Existing investors have interests that don't perfectly align with the company's goals. Some want pro-rata rights. Some accept dilution at the right price. Some have strong preferences about co-investors. The CoS is often the one holding the relationship threads together, making sure every board member feels informed without letting board process slow a time-sensitive deal.
Fundraising is more emotional intelligence than financial intelligence. You need to know your numbers cold. But investors are people making large decisions under uncertainty. They're anxious. They need to trust the team they're betting on. The most important thing you can do in any investor meeting is make the other person feel the company is run by adults with a clear view of reality. Not optimism theater. Not sandbagged sandbagging. A clear-eyed, honest assessment of where you are and where you're going.
That honesty is itself a competitive advantage in fundraising. Most companies oversell. The one that tells the investor "here's what's working, here's what's not, here's our plan" stands out precisely because it's rare. Investors know when they're being managed. They invest when they feel respected.