Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Your first investor meeting went great. They loved your vision, asked smart questions, and said they'd "circle back next week."

Three weeks later, you're still waiting. They're taking forever. You got busy with sales calls. You stopped talking to other investors because these two seemed interested.

This is how fundraises fail.

"There isn't a reason for them to move quickly," Elizabeth told a struggling founder. "There's no investor at the table."

The problem isn't the investors. It's your strategy. Or lack of one.

Why momentum is everything

Fundraising creates a second full-time job. You can't do investor meetings one at a time while running your business. You also can't ignore your business while fundraising. This tension kills companies.

The solution isn't working harder. It's creating urgency through simultaneous conversations.

Investors respond to momentum. When other investors are interested, suddenly everyone wants in. When you're talking to nobody else, even interested investors will slow-roll you.

The tranche strategy that changes everything

Let's say you're raising $700K. Most founders would pitch that as one big round at one valuation. Bad move.

Instead, structure it as tranches. Start with a small tranche at your current valuation. Tell investors you're wrapping up $200K at $3.5M post, and if they want in, the cap will increase after this closes.

Here's how it played out for one founder Elizabeth coached:

Started raising $700K total at $3.5M post. Restructured as a $200K tranche at that valuation. Packed meetings back to back over one week. Small checks started committing at the $3.5M cap. Told everyone the $3.5M tranche was full. 

One fund offered $500K at $4M post. Another fund expressed interest at a higher valuation. Told the second fund the first fund had terms on the table. Asked if they'd do $6M post. They agreed. Went back to the first fund: "If you bump to $7M post, we've got a deal today."

Deal closed at $7M post in under a week. The founder doubled his valuation through momentum and urgency.

"That is how you generate momentum on your round," Elizabeth explained. "It's all about momentum and urgency."

The tactical playbook

Running multiple investor conversations isn't complicated, but it requires discipline. Here's the step-by-step:

Build a massive list. You need 100+ investors to talk to. Use directories like Signal NFX, AngelList, Crunchbase. Build the list before you start outreach.

Batch your outreach. Send 50 emails in one day. Don't send five emails a week for ten weeks. Create urgency through volume.

Schedule meetings clustered together. Book 10 meetings in the same week if possible. Tell late-stage investors that you're in second meetings with others.

Follow up religiously. After each meeting, send a quick email that day. If you don't hear back in 3-4 days, follow up again. Most investors are overwhelmed with emails. They're not ignoring you.

Create an investor CRM. Track every conversation. Note where each investor is in the process. Set reminders for follow-ups.

Send updates to everyone simultaneously. Monthly or bi-weekly investor updates keep everyone warm. Include traction updates, key wins, and asks.

The key is never letting any single investor feel like they have all the time in the world.

Managing the chaos while building

The hardest part isn't the investor conversations. It's doing this while also running your business.

During COVID, Elizabeth and the Hustle Fund team found themselves working more than ever. Portfolio companies needed extra support. The landscape kept changing.

"Between home life being more time consuming and work being more time consuming, basically, you give up sleep," Elizabeth said. "Not every VC wants to do that. Many will not."

The same applies to founders. Fundraising while building means something has to give. Usually it's sleep. Sometimes it's delegating sales calls to your co-founder.

This is why timing your fundraise matters. Don't start talking to investors during your busiest product sprint. Pick a window where you can dedicate serious time to it. Then go all-in.

Navigating different investor types

Not all investors operate the same way. Understanding who you're talking to changes your strategy.

Angels move fast. They're investing personal capital and can decide quickly. Use angels to create initial momentum.

Micro funds can also move quickly if they like what they see. At Hustle Fund, we've done deals in under a week when the fit is obvious.

Larger funds have processes. First meeting with one person. Second meeting with decision-makers. All-partner meeting. There could be many meetings depending on the fund's size.

You can't shortcut a fund's process. But you can try to get all those meetings done as quickly as possible.

Also understand risk profiles. An associate or principal may not have carry, but they could lose their job by championing a bad deal. The decision-maker has upside incentive to take risk because they reap the benefits if it works.

When things slow down

Sometimes conversations stall despite your best efforts. Investors ghost you. Momentum fades.

First, be persistent. Elizabeth used to worry about annoying investors. Now she realizes nobody notices if you ping them three times because they're drowning in emails.

Follow up within a week. Then follow up again 3-4 days later. Don't be an asshole about it, but be direct.

If multiple investors are giving you vague passes, something else is wrong. Maybe your pitch needs work. Maybe the market timing is off. Maybe your traction isn't strong enough yet.

That's when you step back and reassess. Pitch to other founders you trust. Get brutal, honest feedback. Figure out what's not working and fix it.

The final word

Managing multiple investor conversations isn't natural. It feels uncomfortable. You'll worry about being pushy or manipulative.

But the reality is investors respect founders who can create momentum. They want to invest in people who can sell the vision and close the round. Your ability to manage these conversations is evidence of your ability to close sales and partnerships later.

If you want to see how this works in practice, Angel Squad gives you a front-row seat to real fundraises. You'll see how founders navigate multiple conversations, create urgency, and close rounds. Because learning from others' mistakes is a lot cheaper than making them all yourself.