You do not need to finish a course before making progress on your raise. Start with the question you face today, work through an example, and use the exercise to create something your company needs.
Lesson 1 · about 12 minutes
Choose capital that fits your company
Start with what the business needs to accomplish and how it can repay or reward a capital provider. A company with predictable collections and limited expansion needs may have different choices from a product business investing years ahead of revenue. Venture investors typically need the possibility of very large outcomes, while a lender needs a credible repayment path. Grants depend on program eligibility and permitted uses. Compare those requirements with your actual business before putting months into the wrong process.
Example and exercise
Worked example
A fictional services company needs $40,000 to cover signed customer work before payment. That is a timing problem, so the founder first explores deposits and payment terms. A fictional software company needs two years of product investment before dependable cash generation, so it investigates equity and relevant non-dilutive programs instead.
Apply it
Write the milestone, the amount, when cash is needed, and the source of repayment or investor return. Compare at least two funding routes against those facts.
Check your work: You can explain why the selected route fits and what would make you choose another.
Further reading ↗Lesson 2 · about 15 minutes
Decide whether this is the right time to raise
Separate needing money from having a convincing investment case. List the evidence that a customer has the problem, will pay for a solution and will keep using it. Then identify which milestone would reduce the biggest uncertainty. If an investor asks for more traction, ask what observation would change their view instead of interpreting the phrase as a precise target. Keep an alternative operating plan because timing and investor appetite are outside your control.
Example and exercise
Worked example
Ten free pilots and ten paying customers are different signals. A fictional founder records pilot conversion, usage and renewal separately, then decides whether six weeks spent converting pilots would make the raise more credible.
Apply it
Create three claim-and-evidence records. Mark each supported, assumption or missing, and assign an action to the weakest important claim.
Check your work: Each important claim has a dated source or an explicit task to gather one.
Further reading ↗Lesson 3 · about 18 minutes
Connect the ask to a cash calendar
Build monthly cash movements before choosing the amount to raise. Use collection dates, actual expense timing and planned hires. A revenue forecast does not automatically become cash in the bank. Test the slow case: a delayed contract, a later collection or a missed milestone. Explain which assumptions have the largest effect on the funding gap. The workspace models monthly revenue as cash inflow, so adjust those inputs to reflect collection timing.
Example and exercise
Worked example
A fictional company starts with $100,000 and spends $30,000 a month net of collections. Six months consumes $180,000, creating an $80,000 gap before fees or contingency. A three-month delay adds $90,000 if net burn stays unchanged.
Apply it
Save a base plan and a delay scenario. Explain the gap between the two and identify spending you could defer.
Check your work: The ask, milestone date and pitch all use the same assumptions.
Further reading ↗Lesson 4 · about 15 minutes
Explain the market through the customer
Define the first buyer narrowly enough to count and reach. Estimate the number of those buyers and a defensible annual spend, showing where both inputs came from. Keep this reachable segment separate from a broad industry total. Competition includes spreadsheets, internal staff and doing nothing, not just funded startups. A useful comparison explains why a particular buyer switches and what evidence supports that explanation.
Example and exercise
Worked example
A fictional product starts with 2,000 reachable clinics at an assumed $3,000 annual contract. That implies a $6 million segment at full penetration, not a $6 million revenue forecast. The founder still needs evidence for reachable clinics, willingness to pay and distribution.
Apply it
Compare three alternatives by buyer, price or cost, switching reason and source. Label estimates instead of presenting them as measured facts.
Check your work: You can defend the initial segment and describe an actual reason to switch.
Further reading ↗Lesson 5 · about 20 minutes
Build a pitch someone can follow
Give each slide a job in the argument. Start with the customer and problem, show the change your product creates, then support demand, economics, distribution and team with evidence. Make the ask explain what the money changes. An emailed deck needs enough context to stand on its own; a presentation deck can rely more on what you say. Keep claims specific enough to check and make unanswered questions visible in your working notes.
Example and exercise
Worked example
Replace 'customers love us' with a dated retention or renewal observation that you can substantiate. If the sample is small, say so and explain what you are measuring next.
Apply it
Complete the ten-section pitch outline and connect three consequential claims to evidence. Export it and read it without adding spoken explanation.
Check your work: A reader can explain the customer, business, evidence and use of funds after reading the outline.
Further reading ↗Lesson 6 · about 15 minutes
Build a shortlist with reasons
Check stage, sector, geography, check size and whether the investor can lead or follow. Use the investor's current website and published contact instructions where possible. An old portfolio match is a lead, not proof that the fund is still investing. Record unknowns such as reserves, current appetite and conflicts rather than inventing a fit score. Keep your own relationship context separate from public research.
Example and exercise
Worked example
A fund's typical $100,000 check may help fill a round but cannot by itself satisfy a $1 million lead requirement. A sector match with an excluded geography is still a mismatch.
Apply it
Research a small batch, attach source URLs and write one reason for fit and one thing to verify for each name.
Check your work: Every shortlisted investor has a source, next action and a plausible role in the round.
Further reading ↗Lesson 7 · about 12 minutes
Run outreach that you can learn from
Make the message easy to place: what the company does, a relevant result and why this investor may be interested. Ask for a proportionate next step. Start with a manageable batch so you can notice which questions recur and repair unclear explanations. Record actual sends and responses; a drafted message is not a contacted investor. Respect stated submission preferences and stop when someone asks you to.
Example and exercise
Worked example
A founder sends a first batch of eight relevant messages. Three replies ask who buys the product. That is a reason to sharpen the buyer sentence before sending the next batch, not evidence that the business has failed.
Apply it
Draft a first note and a follow-up for one researched investor. Remove any claim you cannot support before sending from your own inbox.
Check your work: The message explains relevance, includes one supported observation and asks for a clear next step.
Further reading ↗Lesson 8 · about 15 minutes
Prepare for the decision after the meeting
Before the call, identify its purpose, the investor's process and the strongest evidence to bring. Practice answering questions about the weakest assumptions without becoming defensive. Afterward, record what was actually said, who owns the next step and when it is due. A friendly conversation is not a commitment. If feedback is vague, ask which specific question needs an answer before the investor can proceed.
Example and exercise
Worked example
Instead of recording 'great call', a founder writes 'partner review on Friday; send the customer cohort table by Wednesday; investor will confirm next step Monday'. That record is actionable even if the outcome is a pass.
Apply it
Prepare three likely questions, conduct a practice answer, then create the follow-up task and requested material record.
Check your work: The meeting has an objective and the next step has an owner and date.
Further reading ↗Lesson 9 · about 18 minutes
Make diligence easier to answer
Maintain a clear index of documents and a queue of investor questions. Check that financial statements, ownership records and customer metrics describe the same period and company. Share sensitive material in stages using your secure file provider's permissions, expiry and access logs. A link in a checklist does not make a document complete or securely shared. Resolve conflicting figures before sending another version.
Example and exercise
Worked example
If the deck says $20,000 monthly revenue and the model says $25,000, label whether one is collected cash, booked revenue or a forecast, and specify the period. Do not silently choose the more attractive number.
Apply it
Review the document index, identify three gaps, and assign owners and dates. Check the recipient permissions on each file you intend to share.
Check your work: Every open request has an owner, a due date and the document or answer that resolves it.
Further reading ↗Lesson 10 · about 20 minutes
Compare offers beyond the headline valuation
Compare ownership economics and control provisions alongside cash, timing and conditions. A valuation number alone does not capture liquidation preferences, option-pool treatment, pro-rata rights or board terms. Use the workspace to organize questions and supported scenarios, then have qualified counsel review the actual documents. Standard forms are a starting point, and changes can alter their effect.
Example and exercise
Worked example
Two offers with the same cash and valuation can leave different outcomes if one changes the option pool before investment or includes different preferences. Record the exact clause and question rather than assuming equivalence.
Apply it
Enter two offers, list the clauses you do not understand and prepare a question list for counsel. Reconcile the ownership calculation to the final documents.
Check your work: You can explain the main tradeoffs and unresolved questions without calling a simplified calculator a legal answer.
Further reading ↗Lesson 11 · about 15 minutes
Track the close through received cash
Keep verbal interest, document execution and received funds in separate states. Confirm required approvals and signatures with counsel, maintain a closing checklist and reconcile receipts against your own bank records. Verify payment instructions through an established independent channel. The workspace is a record of the process, not a payment system or a substitute for legal completion.
Example and exercise
Worked example
A fictional round has $100,000 verbal, $200,000 signed and $150,000 received from different investors. Only the $150,000 received belongs in the actual cash balance. Update each investor record as its state changes, rather than adding duplicate rows.
Apply it
Create one record per commitment, attach a reference to the supporting record and update the stage as the close progresses.
Check your work: Received funding matches actual receipts and outstanding conditions have owners.
Further reading ↗Lesson 12 · about 12 minutes
Keep the relationship useful after the raise
Use a consistent reporting period and metric definitions. Explain progress against the milestone the round funded, what changed, cash and runway assumptions, and specific ways investors can help. Report setbacks with the action being taken rather than hiding them or adding vague optimism. Keep confidential details appropriate to the audience and use the same underlying figures as the operating plan.
Example and exercise
Worked example
A useful ask might identify the buyer role, company size and geography for an introduction. 'Please help with sales' leaves the investor to invent the next step.
Apply it
Draft the first investor update with a dated metric, an honest challenge and one specific ask. Schedule the next preparation task.
Check your work: An investor can understand progress and act on the request without another explanation.
Further reading ↗These are original TRM lessons. Linked outside resources provide further reading; their publishers are not TRM partners or endorsers.
