Two founders’ contrasting raises show how customer conversations, investor research and early relationship building can make fundraising more focused.
Founders who feel certain they can raise capital usually have spent months learning what investors expect. That preparation shapes the business as well as the fundraising process: it helps founders understand their market, test assumptions and build relationships before they need a check.
A few years ago, three founders who had just completed Series A rounds told me they had each put their chances of raising at 100% before starting. Their confidence wasn’t a guess. They had built relationships with venture capitalists over the previous year or two, understood the bar for their market and planned their execution around reaching it.
That experience contrasts with founders who bring an early idea to a meeting and ask whether it seems fundable. The difference shows up in the questions they can answer. A prepared founder can explain what they intend to do and why. A founder still guessing is more likely to ask someone else to assess the plan.
Build knowledge through conversations
In a recent quarterly How I Raised session with Qapita, our favorite cap table management tool, Advait of Elm AI and Manthan of Destro described how they prepared. Advait’s company spun out of Cornell Tech. Destro builds software that directs groups of 25 to 50 warehouse robots.
Before Elm AI had become a company, its founders tracked one key measure: how many people in their industry they spoke with each week. They held 100 to 200 meetings, compared outreach totals and kept a list of hypotheses. Each conversation helped confirm an idea or gave them reason to discard it.
That routine gave the founders a practical education in their market. It also reflects a broader point: talking with founders who have raised from established venture firms can help a team understand how fundraising works. Without those conversations, founders may discover basic expectations only after the process is underway.
For example, a founder should be able to state a target amount and explain the calculation behind it. That means mapping the next 24 months of planned work and understanding how much additional capital the market might support. Manthan went out with a $4 million target, a baseline and a ceiling, rather than offering a loose range and waiting for investors to choose.
Know who to approach and when
A broad list of anyone willing to meet may seem like a start, but it can leave founders unprepared to identify a good fit. Advait described his first fundraising effort as “spray and pray.” It took more than six months, and he didn’t know investors’ typical check sizes or that securing a lead investor would matter.
For a later round, he changed the approach. He expected to raise in the fall, after the company reached seven figures in revenue, and traveled to San Francisco months earlier to meet founders rather than pitch investors. He wanted introductions from people who knew and trusted him. The plan was to start relationships early, share progress and arrive in the fall as a familiar name.
The process moved faster than expected. An investor came into a friend’s office while Advait was there, and the round was oversubscribed within a week. The chance encounter was helped by the groundwork: Advait had already been building a network of founders who could make introductions.
Research also helps founders decide which investors to contact. They can look for firms that have backed companies at a similar stage, learn the size and type of checks those firms write, and find out whether they lead rounds. Conversations well before fundraising can reveal which one or two investors are especially relevant to a company’s field.
Set the bar before the process starts
Prepared founders have a clearer view of the progress investors will expect. They’ve seen what fundable companies in their market look like and can set operating goals accordingly. Manthan understood what his seed investors wanted to see and prepared to meet the expectations of the next round.
They also plan for a no. One approach is to speak first with lower priority investors, using those meetings to practice and learn, then approach the most sought-after firms after receiving a term sheet. A founder may also hold back a meaningful customer milestone or other piece of progress to share later if interest needs to turn into commitment.
The calendar matters too. Starting when cash is nearly gone leaves little room to learn or build relationships. The founders in these examples began conversations about a year ahead, sometimes explaining that they weren’t raising yet. That gave them time to understand investor expectations before asking for capital.
Advait’s first and second rounds show what that preparation changed. His first took six-plus months and hundreds of meetings, with little understanding of check sizes or the need for a lead. The second involved three investors, all of whom participated, and was oversubscribed within a week. It was the same founder and company, with a year of conversations in between.
Manthan took a similar path before Destro’s seed round. He held about 20 calls while telling investors the company wasn’t raising yet. Warm introductions came from his pre-seed investors. He spoke with lower priority firms first to learn how the market viewed the opportunity, then approached the most sought-after firms once he had a term sheet. He saved the close of Destro’s second enterprise customer as what he called the “closing blow.” The company initially sought $2 million, received commitments above $14 million and accepted $8 million.
Preparation is part of operating
After making 105 first checks, I used to treat fundraising skill as separate from the ability to run a company. I thought a founder could be unprepared to raise and still be a strong operator. These examples changed my view: the habits that make a founder more prepared to raise also help them run the business.
Manthan said Destro still operates as though “tomorrow we won’t exist,” despite having years of runway. The team keeps learning rather than taking its position for granted. That means speaking with customers to understand what might lead them to spend more, and with other people who can help the company grow.
There’s no universal number of conversations a founder should schedule each week. The useful measure is whether the team is steadily learning from its market, customers and peers. By the time a raise begins, that work should have clarified the company’s goals, its likely backers and the milestones that can support its case.
