Startup Fundraising Prompts

18 prompts 9 guides
topic

The share of seed-funded companies reaching Series A within two years halved between the 2018 and 2022 cohorts. Raising is now the exception, and the advice mostly hasn't caught up.

The bar moved and most of the advice didn't

Carta's cap-table data records the change plainly. Of companies that raised a seed round in Q1 2018, 30.6% reached a Series A within two years. For the Q1 2022 cohort the figure was 15.4%. The path narrowed by half.

At the same time the bar for clearing it rose. Median ARR at Series A now sits around $3 million — a level that would have been a strong Series B story a decade ago, and that many founders are still being advised they can skip.

Rounds got bigger and rarer simultaneously, which is a specific and awkward combination. It means the median seed-funded company is no longer on a path to a Series A; it is on a path to profitability, an acquisition, or a shutdown, and the sooner that is planned for the better the outcome tends to be.

Three consequences run through this pack.

Raising is now the exception, not the milestone. So the first prompt asks whether to raise at all rather than how.

A round has to be sized to a milestone that clears the next bar. Money that buys eighteen months and gets you to $1.2M ARR has bought you a hard conversation, not a runway.

Every founder number will be checked against a dataset the investor has and you do not. Investors see hundreds of companies a year and have benchmark data on all of them. A number that cannot survive that comparison damages more than the number.

Decide whether, then how much

Decide Whether You Should Raise Money at All works through what venture capital actually requires of a business — a plausible path to a very large outcome, on a timeline someone else sets — and whether that describes yours. Plenty of good businesses fail that test, and building one of them on venture terms is how a healthy company becomes a failed one.

Work Out How Much to Raise and What It Buys You ties the amount to specific milestones with dates and a defensible bridge to the next round, rather than to a number that sounded normal at a conference.

Work Out Your Runway and How to Extend It and Decide How to Fund a Gap or a Growth Push cover the arithmetic underneath, and Apply for a Grant or Non-Dilutive Funding covers the option most founders skip because it is slower and less exciting. Given a 15% graduation rate, slower and less exciting deserves more consideration than it gets. The business finance pack covers the operating side of the same numbers.

Never produce a number you cannot defend

The editorial rule for every quantitative prompt here: no top-down TAMs, no hockey sticks, and every assumption labelled with its source.

Size Your Market Without Making Up a TAM builds bottom-up from customers, price and reachable segments. A top-down 1% of a $50 billion market is the single fastest way to signal that you have not done the work, because the investor has seen that slide several hundred times.

Build a Financial Model an Investor Will Believe makes the assumptions the visible part of the model. The projection is not what gets evaluated — the assumptions are, and a model whose growth rate is unexplained is a model nobody reads twice.

The narrative and the process

Write the Pitch Deck Narrative Before You Design a Slide enforces a useful order. Design work on a deck whose argument does not hold is expensive procrastination.

Build an Investor Target List and Work Out Who Actually Fits treats fundraising as a sales process with a qualification stage — check size, stage, sector, portfolio conflicts, and whether the fund is actually deploying. A meeting with a fund that cannot write your cheque is a day gone.

Write an Investor Cold Email That Earns a Meeting is the outreach artifact. Prepare for the Questions That Kill Pitches builds the list you are hoping to avoid, on the reasoning that every founder has two or three questions they cannot answer well and investors find them within ten minutes.

Prepare a Data Room and Survive Diligence covers the stage where deals quietly die — not from a disqualifying discovery, but from slow, disorganised responses that read as an operational warning.

Write an Investor or Lender Update That Builds Confidence is the highest-leverage recurring document a founder writes. Investors fund people whose bad news they trust.

Terms, dilution, and equity between founders

Dilution and control are priced in the terms, not the valuation. A higher headline valuation with a larger option pool carved out pre-money, a participating preference, or a stack of prior post-money SAFEs converting at once can leave you owning less than a lower-valuation clean deal would have.

Understand What a Term Sheet Actually Costs You explains the economics of the terms that matter, and Work Out Your Dilution Before You Sign Anything makes you run the actual cap table through the conversion rather than trusting the summary.

Split Equity With a Co-Founder Without Wrecking It covers the conversation that is hardest early and catastrophic late, including vesting and what happens if someone leaves.

Handle a Raise That Isn't Coming Together is the prompt this cohort data makes necessary. Most raises do not come together, and the difference between a company that survives that and one that does not is usually how early it stopped pretending otherwise.

Where this stops

Every prompt in this pack that touches terms, equity, or securities explains the economics and stops at the point where you need a startup lawyer. Term sheets, SAFEs, option pools, co-founder agreements and vesting schedules are legal instruments with jurisdiction-specific consequences, and the cost of getting them wrong is measured in years. Nothing here is legal, tax, or investment advice, and no prompt will invent a benchmark, comparable, or valuation for you.

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The 18 prompts in this pack

Handle a Raise That Isn't Coming Together

Diagnoses why a round has stalled and lays out the real options while you still have cash to choose between them. Use it when you're months in with...

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Apply for a Grant or Non-Dilutive Funding

Works out which non-dilutive funding you actually qualify for and writes the application against the assessor's criteria rather than your own enthu...

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Prepare a Data Room and Survive Diligence

Assembles what investors will ask for, finds the problems before they do, and decides how to disclose the ones you can't fix. Use it as soon as a t...

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Work Out Your Dilution Before You Sign Anything

Models what you'll actually own after this round, the option pool, and the rounds after it, so ownership isn't a surprise at exit. Use it whenever ...

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Understand What a Term Sheet Actually Costs You

Translates a term sheet into what it means for your ownership, your control, and your outcome in the cases that matter. Use it before you respond t...

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Prepare for the Questions That Kill Pitches

Surfaces the questions that will expose the weakest part of your story and builds answers that hold up under a second and third follow-up. Use it t...

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Write an Investor Cold Email That Earns a Meeting

Writes the short, forwardable outreach email that gets a first call, and the intro request that gets a warm path instead. Use it for every investor...

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Build an Investor Target List and Work Out Who Actually Fits

Turns a scattershot outreach plan into a researched, sequenced list of investors who genuinely invest in businesses like yours. Use it before sendi...

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Write the Pitch Deck Narrative Before You Design a Slide

Builds the argument a deck has to make, in order, so the design stage has something to carry. Use it before opening a template.

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Build a Financial Model an Investor Will Believe

Constructs a driver-based financial model with assumptions you can defend individually, instead of a spreadsheet that grows 20% a month because it ...

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Size Your Market Without Making Up a TAM

Builds a bottom-up market size from counts and prices you can defend, and kills the top-down percentage-of-a-huge-number slide. Use it before any p...

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Work Out How Much to Raise and What It Buys You

Sizes a round from the milestone it has to reach rather than from a round name, and tests whether that milestone clears the next bar. Use it before...

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Split Equity With a Co-Founder Without Wrecking It

Works through a founder equity split and vesting terms while the conversation is still easy, covering the scenarios that break partnerships later. ...

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Decide Whether You Should Raise Money at All

Tests whether venture funding is the right instrument for your business, or whether debt, revenue, or patience would serve you better. Use it befor...

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Write an Investor or Lender Update That Builds Confidence

Writes the periodic update in a consistent shape, leads with the state of the business, puts the bad news early with a response attached, and weigh...

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Decide How to Fund a Gap or a Growth Push

Checks whether you have a timing problem or a profitability problem, compares every realistic funding option on true annualized cost and downside, ...

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Work Out Your Runway and How to Extend It

Calculates how many months of cash the business has under three scenarios, works backward to the date you must decide by, and ranks every extension...

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Raising Venture Capital

Raising money for a start up. Here is a strategic prompt to help you develop a compelling venture capital pitch.

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