What a $1B+ Fundraising Career Taught Sasha Orloff About Winning Investor Trust

The most important fundraising skill may be less glamorous than a polished pitch deck: knowing exactly what is happening inside the business. Sasha Orloff, the founder of Puzzle, has helped raise more than $1 billion across multiple fintech ventures. His advice is straightforward: venture capitalists do not expect an early-stage company to be flawless, but they do expect its founder to understand reality—and explain it clearly. 12

That means knowing which parts of growth are repeatable, how quickly the company is using cash, what its margins say about the business model, and which risks could change the outcome. Fundraising is therefore not only a sales exercise. It is also a test of financial command, operating discipline, and trust.

The numbers founders should know before a pitch

A top-line revenue figure is only the beginning of the conversation. Investors want to understand the quality and durability of that revenue, as well as the cost of producing it. Orloff highlights several areas founders should be able to discuss without relying on someone else to interpret the data: 13

• Revenue growth and quality: Is growth recurring, concentrated among a few customers, or dependent on one-off activity?
• Burn and runway: How much cash is the company using, and how long can it operate under its current plan?
• Margins: Does each sale contribute to a business that could become economically attractive, or does growth increase the company’s losses?
• Sales efficiency: How much does it cost to acquire customers, and how effectively does the company convert spending into revenue?
• Profitability and its path: If the company is not profitable, what operational changes or scale effects could move it toward sustainability?

The point is not to present every metric as positive. It is to connect the metrics into a coherent explanation. Fast growth accompanied by deteriorating efficiency tells a different story from fast growth with improving margins and a clear path to repeatability.

Fundraising expectations change at every round

A founder should not use the same evidence at every stage. Orloff’s framework is a useful shorthand for how the investor question evolves: 2

• Pre-seed: Can this team build something investable?
• Seed: Do customers care, and is there evidence of early product-market fit?
• Series A: Has the company found a credible, measurable way to grow?
• Series B and later: Will additional capital make the company more valuable through scalable economics, operating maturity, and stronger execution?

At the earliest stages, investors may spend more time evaluating the team, the insight behind the product, and early validation. As the company grows, the burden shifts toward evidence: customer and revenue quality, repeatable acquisition, financial controls, and the ability to deploy capital without losing operational discipline.

This is not a rigid checklist for every startup. The relevant proof depends on the business model and market. But the underlying progression is consistent: each round requires founders to replace more assumptions with measurable evidence.

Waiting until the cash is almost gone weakens the process

Fundraising becomes more difficult when it starts as an emergency. If a company approaches investors only when its cash is nearly exhausted, the founder has less time to run a process, compare offers, or reject terms that do not fit. That urgency can weaken negotiating leverage, affect valuation, and potentially put a term sheet at risk. 13

Starting earlier does not guarantee a successful round. It does create options. With more runway, founders can identify suitable investors, develop relationships before they need capital, improve weak metrics, and prepare answers to likely diligence questions. The goal is not to fundraise constantly; it is to avoid making a high-stakes financing decision under avoidable time pressure.

A data room is a test of trust

Orloff has described nearly losing a term sheet because his data room was not ready. The lesson is larger than document organization: diligence materials signal how the company handles foundational responsibilities. If financial records, compliance information, contracts, or ownership documentation are incomplete or inconsistent, investors may question what else they have not been shown. 13

A practical data room should be assembled before a round is urgent. Depending on the company’s stage, that can include:

• financial records and a current operating model;
• revenue and other material contracts;
• people and employment-related contracts;
• cap-table information; and
• relevant accounting, tax, and compliance documentation. 310

The exact scope will vary, especially between a pre-seed company and a later-stage business. What should not vary is the standard: numbers should reconcile, ownership should be clear, and the founder should know where the gaps are.

Preparation also makes the founder’s answers faster and more precise. That can reduce friction during diligence and help investors assess execution risk with greater confidence. 13

Honesty is more credible than a perfect story

Investors already understand that startups have weaknesses. Hiding a problem can make it more damaging when diligence uncovers it. A stronger approach is to identify what is not working, quantify the exposure where possible, and explain the plan to address it. 13

That does not mean leading with every concern or turning a pitch into a list of failures. It means avoiding claims the data cannot support. A founder who can say, “This is the weak point, this is what caused it, and this is how we are measuring improvement,” demonstrates a closer relationship with the business than one who presents an unrealistically flawless picture.

The same principle applies to metrics. Founders should understand not only the headline number but also its definition, data source, limitations, and relationship to the company’s broader economics.

Why Orloff built Puzzle

Orloff’s own experience managing finances while scaling companies helped shape Puzzle, which he describes as an AI-native accounting platform designed to give founders more timely financial visibility and simplify fundraising preparation. 123

That origin story reflects a broader shift in how startup finance can be used. Accounting is not only a record of what happened at the end of a reporting period; timely financial information can help leaders monitor burn, runway, revenue performance, and operating risks while decisions are still being made.

AI’s potential contribution is to make financial information more continuously useful—for example, by helping organize business data, surface changes sooner, and support faster reporting and diligence preparation. The sources describe this as a direction and product promise, not a guarantee that every accounting task is automatically solved. 123

A founder’s fundraising checklist

Before beginning investor meetings, founders should be able to answer five questions:

1. What is driving revenue growth, and how much of it is repeatable?
2. What are the company’s current burn, runway, margins, and sales-efficiency trends?
3. What does the next financing round need to prove that the current round did not?
4. Can an investor review the company’s financial, contractual, ownership, and compliance records without encountering avoidable confusion?
5. Which weaknesses are real, and what specific evidence would show that they are improving?

The central lesson from Orloff’s fundraising experience is not a secret valuation formula. It is a discipline: know the business beneath the deck, begin before the cash crisis, prepare for scrutiny, and communicate risk plainly. Those habits can create the confidence and negotiating leverage that presentation polish alone cannot. 13