Most founders start preparing for a raise by building a pitch deck. By the time the deck exists, the questions that decide the outcome have usually already been answered, correctly or incorrectly, months earlier. Episode 17 of Call to the Bullpen is about that earlier work: the unglamorous preparation that determines whether an investor meeting is a conversation or a formality.
Can fractional leadership help us prepare for investor meetings?
Yes. Experienced fractional or advisory leadership helps a company prepare for investor meetings by pressure-testing the market sizing, aligning the financial plan to the business plan, and cleaning up the cap table before diligence begins. Investors fund proven models over ideas, and a team that has raised capital before knows which proof is missing.
The value is less about polish than about knowing what gets asked. Someone who has sat on both sides of the table can tell you which of your numbers will not survive a follow-up question, which is a cheaper lesson to learn in a rehearsal than in the meeting.
The starting point is not the deck at all. “It’s a great idea, but what problem are you solving?” says Ted Stann, co-founder of Boardroom Bullpen, a veteran of the St. Louis startup ecosystem and a former adjunct professor at Washington University’s Olin Business School, who has raised over $300 million in capital across his career. On the episode he makes the point repeatedly: there are a lot of good ideas in the market, and the ones that get funded are the ones attached to a problem someone will pay to solve.
That distinction reframes everything downstream. If the business exists to solve a specific, expensive problem, then market sizing, differentiation, and financial projections all become arguments about that problem rather than decoration around an idea.
What do investors actually evaluate before writing a check?
Investors evaluate the team at least as heavily as the product, and often more heavily.
Ted relays a piece of advice he received early from a venture capitalist that has held up across his career: “You can have an A plus product and a B management team, and you’re not as likely to get funded as if you had an A plus management team and a B product.” The logic is straightforward. A strong team can fix a mediocre product. A mediocre team usually cannot rescue a strong one, and the investor has no mechanism to swap the team out after the wire clears.
Experience counts in that assessment, but it is not the whole of it. Investors are also underwriting what happens after the money arrives. As co-host Clint Overton frames it on the show, if the company already had it figured out, it would not be raising. The investor needs confidence that the team can convert capital into revenue, and specifically into revenue that repeats.
This is also where the market has shifted. Ted was raising money during the dot com era, when a compelling idea could attract funding on its own. After the bubble burst, he says, the expectation changed to wanting more meat on the bone, and the 2008 crisis tightened it further. His read on the current environment is that raising has been difficult since roughly the first quarter of 2022 and has not meaningfully loosened since.
How do you size your market for an investor pitch?
Market sizing works through three nested numbers, and investors expect all three.
| Term | What it measures | Ted’s banking example |
|---|---|---|
| Total addressable market (TAM) | The full dollar size of the problem you are solving | $20 billion |
| Service addressable market (SAM) | The slice of that market your solution can actually reach | $500 million |
| Service attainable market (SOM) | What you can realistically capture in three to five years | $10 million to $50 million |
The third number is the one investors scrutinize, because it is the only one that constitutes a claim about your company rather than about the industry. A $20 billion total addressable market is a fact about banking. A $15 million attainable market in three years is a forecast you are personally accountable for.
The work behind those numbers matters more than the numbers themselves. Clint pushes back on the shortcut version directly, describing founders who run a search on ChatGPT or Claude or Google and throw the result on a page. A sourced, defensible figure survives the follow-up question. A borrowed one does not, and the follow-up question is where the meeting is actually decided.
Where should your market research actually come from?
Three sources, according to Ted, and each answers something the others cannot.
Competitors. Study what is already in the market to find the gap you are filling. This is where your differentiator comes from, and it needs to be a real one. Ted is blunt that cost should never be your differentiator. It can be one of several, but a thesis built on undercutting the market’s pricing is very hard to get funded, because price is the easiest thing for an incumbent to match.
Potential customers. Take the differentiation you found and test it against the people who would pay for it, including your existing customer base if you have one. This is the difference between believing you have found a gap and confirming it.
Investors themselves. This is the source most founders skip, and it is the one Ted singles out. Venture capitalists see every company competing in your space and will tell you what they are seeing. The way to unlock that is not to pitch. It is the best fundraising advice he received: ask for advice and they will give you money, ask for money and they will give you advice.
That is not a rhetorical flourish. It is a practical sequencing instruction. An early conversation framed as advice-seeking gets you market intelligence, a read on the firm’s thesis, and a relationship, all before you need the answer to be yes.
Why does coachability matter more than your pitch deck?
Because the investor is buying a multi-year working relationship, and they are assessing it in the room.
Founders often arrive believing they need to project total command, that they should be the alpha in the conversation. Clint describes the opposite instinct as the one that actually lands: a balance of humility and vulnerability, because the investor wants to see that you are coachable. They are betting on you, and they want evidence you will take feedback once their money is in the business.
Ted extends it past the founder. Coachability is assessed across the whole leadership team, not just the person presenting. “I don’t have all the answers. I am willing to accept advice,” is how he characterizes the posture that works, and he notes that when founders and executives have it, the conversations get easier for everyone.
There is a human dimension underneath it that Clint thinks founders forget. Investors want a return, but they also want to feel additive. Someone writing a check with decades of relevant experience wants to contribute more than the check, and a founder who signals there is nothing to contribute has removed part of the reason to participate.
How to get fundraising-ready: a six-step checklist
Write down the problem, not the idea. State the problem in the market, who has it, and what they currently pay to deal with it. Every other document you produce should trace back to this one.
Build TAM, SAM and SOM from sourced research. Show your work. Assume every figure gets a follow-up question and prepare the answer before the meeting rather than during it.
Define a differentiator that is not price. Identify the gap from competitor research, then confirm it with real customers before you present it as validated.
Marry the business plan to the financial plan. Hiring assumptions, quota assumptions, and revenue projections should reconcile to each other line for line.
Talk to investors early, asking for advice. Use those conversations to understand each firm’s thesis and to learn what they are seeing in your market. Do this before you need a decision.
Get an experienced advisor in your corner. Someone who has been through a raise, and often a business attorney alongside them, so that the structural decisions you make early do not restrict you later.
FAQ
Is fundraising readiness different for angel investors than for venture capital?
The principles are consistent across investor types, but the proof differs. Angel and friends-and-family money typically funds proving the model. Venture capital typically funds scaling a model that already works. Both expect a defined problem, real market research, and a credible team. What changes is how much evidence of repeatable revenue you need in hand.
Do companies that already have revenue need fundraising readiness work?
Yes. Fundraising readiness is not exclusive to pre-revenue startups. A company five years in, generating revenue, and raising growth capital faces the same diligence on market sizing, differentiation, team, and financial planning. In some cases the scrutiny is higher, because there is now a track record to examine.
How do we identify and mitigate business risks before diligence?
Work backward from the questions an investor will ask. Customer concentration, unproven conversion assumptions, gaps in the leadership team, and structural issues on the cap table are the usual ones. Identifying them yourself and having a stated plan is far stronger than being surprised by them in a diligence call.
How do I engage fractional executives to help prepare for a raise?
Fractional executives are typically engaged on a monthly retainer for a defined scope, which for fundraising preparation usually means financial planning, market analysis, and readying the company for diligence. The useful qualification to screen for is direct experience raising capital at your stage and with your type of investor.
Listen to the full episode
Episode 17 of Call to the Bullpen also covers cap table structure, the difference between participating and non-participating preferred stock, what separates a good investor from a checkbook, and why repeatable revenue determines which investor you should be talking to. Listen at https://www.calltothebullpen.com/