The truth about raising your next round 💸

What founders told me about fundraising that works

Last week I shared how a top investor judges pitches, which exposed a way of thinking that most founders never hear directly. The reaction to that piece made something clear: you wanted the other side of the story too.

So I went back through more than fifty Millennial Masters interviews to pull out the most practical fundraising lessons founders shared on record.

These conversations revealed how momentum really forms, how pitches improve under pressure, and how early decisions can shape a company for far longer than most founders expect. 👇🏻

Access usually arrives before opportunity. Illustration: ImageFX/MM

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The doors that open a round

Founders return to this principle repeatedly because it shifts the atmosphere inside the first meeting in a way that cold outreach rarely achieves.

Tom Wallace-Smith captured this clearly when he told me, “The difference in cold introductions versus warm introductions is like night and day. A warm introduction, that person’s almost avowed for you.”

That psychological shift creates room for substance before scepticism, and it shapes the entire tone of the conversation in ways most first-time founders underestimate.

Those who begin without a network often build one through disciplined effort rather than inherited access. Yehong Zhu explained how she created momentum by finding lists of female founders and investors and adding them on LinkedIn.

This helped her open conversations without any established base. “I didn’t have a preconceived network.” The method was slow, but it allowed her to build genuine familiarity long before she reached out for capital.

Other founders rely on consistent visibility between rounds. Kevin de Patoul told me that early relationships form during the quiet years when no raise is underway.

Investors become more receptive when they already know the founder’s name and trajectory, which reduces the friction that usually slows early conversations.

A different kind of visibility shaped the path for Nick Holzherr, whose appearance on The Apprentice created a shortcut into investor inboxes. “I could basically send them an email and say, ‘Hey, I’m Nick, I was on the Apprentice,’” which gave him an entry point that many founders spend years trying to establish.

Some founders also talked about meeting investors in places that had nothing to do with formal fundraising. Tom Wallace-Smith met future backers at a house party in Virginia during a conference in Washington, which pushed his round forward in an unexpected way. It served as a reminder that physical rooms still matter, even in a world shaped by online outreach.

Fundraising still carries setbacks. Lara Varjabedian responded with a habit that kept her moving. “Every time some bad news happens, I reach out to ten potential partners or ten potential investors.” This approach protected her from periods of stagnation and widened her net at the moments she needed it most.

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What improves a pitch for real

You rarely arrive with a polished pitch. You refine it through many conversations that serve as low-pressure testing grounds.

Tom Wallace-Smith described how early meetings with investors who were not an ideal match helped him identify weak explanations before the stakes increased. Those iterations allowed him to clarify the story until it carried the weight he needed.

Yehong Zhu used this principle to get founders to expose their earliest deck to someone willing to offer unfiltered critique. “Have them just give you the most brutal feedback possible.” If you treat those moments as working sessions rather than performances, you will progress faster than those who wait for a perfect draft they never truly finish.

Investors pay attention when the significance of the problem becomes unmistakable. Tom said, “The stakes have to be high.” Investors listen for the real consequences behind the problem and respond when the founder can explain why the world needs the solution now rather than later.

Traction often intimidates early founders who lack revenue. Nick Telson-Sillett reframed this completely. “If you haven’t sold $1 yet, but you come to me with interviews of a hundred people you’ve spoken to, that’s traction at pre-seed.” Insight becomes proof when sales remain distant.

Differences in investor psychology became clear in my conversation with Joshua Western, who raised across several regions. “By an American venture capital firm, I’ll be asked, how big can this be? A British investor will ask me, if everything fails, what’s the value left in the company?” He learned to address each instinct directly because the pitch lands more cleanly when it aligns with the investor’s natural way of evaluating a company.

Tom Wallace-Smith found that even the investors who passed often made introductions to others, which helped him refine his pitch and widen the surface area around his round. These early calls rarely lead to immediate money, yet they often create the movement that matters later.

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Choosing your path to capital

Crowdfunding attracts founders who care about community as much as capital. Liam White described how this approach brings supporters into the journey early. “You get this whole bunch of evangelists who come on board with the journey.”

He also explained why campaigns require offline preparation. Raising thirty to fifty percent of the round before launch helps the public campaign gain momentum the moment it appears.

Some founders prefer private investment because it minimises unnecessary friction. Sam Holmes explained the core reason when he said, “Private comes a lot cheaper.” Commission fees reduce efficiency, especially for companies that expect multiple rounds or longer time horizons.

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The reality of the early years

The earliest stage forces founders to stretch every resource they have.

Rob Smith worked demanding construction shifts while reserving one day each week for product development, which kept his idea alive while he saved for the first build.

Some journeys require heavier personal choices. James Fleming described how he and his wife sold valuable items to keep their marketing active. “I actually had to sell my watches. My wife sold her gold just to keep the marketing running.” That decision altered their relationship with risk and forced a deeper level of commitment.

Several founders also shared how unexpected encounters turned into investment conversations once they were honest about the pressure they were carrying. Lara Varjabedian met one of her early angels at an event and closed the commitment over coffee the following week.

These small moments mattered because they arrived when the business had no safety net, and the relationship gave her enough confidence to keep moving.

Structural decisions have equally lasting consequences. Gus van Rijckevorsel reflected on his early failure with complete clarity. “A massive cap table with a very large valuation. Never do that.” Those decisions restricted his company’s freedom and created problems that could not be undone.

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The raise is only the opening move

Once a raise completes, founders carry a responsibility to maintain regular communication. Nick Telson-Sillett views silence as a significant issue. “I think it’s criminal for founders that don’t speak to their investors.”

He expects monthly updates that explain progress, problems, and specific requests. He also sees a founder’s background as a strong indicator of future behaviour. “The more challenging stories they’ve had to overcome will probably make them a better founder.”

Tom Wallace-Smith believes the venture path requires continuous preparation, and he told me there is “not really a pause” once you begin. He treats each future raise as a work package he plans ahead of time, which helps remove pressure when cash eventually tightens.

Others caution against turning this mindset into a cycle that erodes trust. Nick Telson-Sillett warned that the pattern of “spend all the money, raise again, spend all the money, raise again” eventually collapses because investors recognise the instability behind it.

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A strong fundraising journey in 2026 begins long before the first investor meeting.

If you take this seriously, begin now by building the relationships that will support you later, placing yourself in the rooms where opportunities appear and shaping a pitch that improves each time you explain what you are building.

These habits create the familiarity investors recognise instantly and make the raise feel like a continuation of a real conversation rather than a sudden request for capital.

This preparation does not need to be loud, but it does need to be steady.

Every early introduction, every small discussion and every quiet refinement to your pitch builds the foundation your future round will rely on.

If you begin this work now, the decisions you make in 2026 will feel sharper and far more controlled than anything assembled at the last minute.

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