Josh raises a Series A (and becomes a monster)

Season three Jess is not season one Jess. Same goes for Josh. Raising $10 million will do that to a person.

We'd been running on instinct for years. Then someone goes "show us the proof."

Josh ended up in this exact situation while trying to raise the Series A. For most of 2025, we ran on vibes. Mostly inbound. No outbound. Some paid, and it worked. There was never any reason to track input against output till the investors came into the picture.

We had to do what I now call, very scientifically, a Deep Ass Financial Dive™. It worked.

In this episode, Josh gets into what it takes to raise a Series A.

Spoiler: it's not fun.

But he came back with a pretty defined playbook. You'll hear how we turned vibes into figures — and how I, and the entire leadership team, learned to stop asking for permission when Josh wasn't around to give it.

What you’ll learn 

• Why a Series A looks different from how it's sold online
• How to build and rebuild customer proof after a pivot
• How to stop asking for permission when the CEO is out of the room
• The three phase approach to navigating the fundraising circuit
• How to make your PR your own — by ditching the press release for a 90s sitcom video
  

TOP THREE TAKEAWAYS

Takeaway 1: Raising a series A is peak sales and rejection‍

Fundraising has this rep for being grueling — even that undersells it. What nobody puts in those celebratory posts on LinkedIn is that it's a demoralizing process.

Josh says it's like showing up to the lunch table asking, "am I pretty and can I sit with you?" and they look at you and say, "you're disgusting."

So, how did he survive it? Three phases.

Phase 1: Pitch to investors you don’t want money from

This was basically a week of meetings with investors he had zero intention of taking money from.

It was everyone from wrong-fit funds to people whose partners showed up five minutes in and were obviously just hitting their quotas. At some point, he was thinking, "Do you want me to just pitch your EA?" Fine. Because that's the entire point of this phase — you bomb where it doesn't count, collect the feedback, and sharpen the pitch before heading into rooms filled with the kinds of investors you’re after.

Phase 2: Get the whisper game in motion

If there's one thing this process confirmed, it's that high school never ends. You want to meet an investor, but you can't seem too eager. So, Josh did warm intros through existing investors and let word travel through the right networks.

Then what? Sit tight.

Not an easy wait. What if no one talked? What if week three arrived and the inbox was dead? Perfectly valid concerns.

But right in the middle of week two, fifty inbounds in a single week from people who'd simply heard something was happening.

Phase 3: Manufacture scarcity and hit the road‍

Josh took every conversation showing real interest from phases one and two and hit the cities. Mostly San Francisco, some New York and Boston.

The goal? Make it look like everyone wanted a piece. "I've got one slot left in New York on Tuesday." He didn't have a flight to New York. The name of the game is supply and demand.

Then people start dropping out. It was a pass here, a "not really our space" there. Then by week four, he's down to three serious VCs. If any of them walk, it's square one all over again. At that point, the timeline was uncertain.

It could be done next week.

Could also be eight more months.

No one knew. It was neither.

Vector closed $10 million from SignalFire and HubSpot Ventures. As it turns out, the lunch table had room after all.

Takeaway 2: Even the investment war front needs an intermission

It's week four. Josh is somewhere over the middle of the country. Third flight in two weeks. Two meetings behind him. Two more ahead.

Jess said she felt like she was waiting for a telegram.

She got one.

Ye olde English prose from a plane at 3am. Nobody sends a message like that after weeks of flights, pitches, and rejection because they're having the time of their life.

Sometimes the only way to survive something demoralizing is to make it funny.

Takeaway 3: Sometimes the best thing a founder can do is disappear

It turns out raising a Series A leaves very little time for answering Slack messages. That meant a lot less "Josh, what do you think?" The team and I had to stop asking for permission and start making bigger decisions.

When Josh came back and looked through everything, his reaction was pretty simple. There wasn't a single decision he would've done differently.

That confirmed something for a lot of us. Me in particular. We actually knew what we were doing.

And if you're a marketer reading this, the point isn't "tell your CEO to ghost you for a month and see what happens." Just notice what changes when the go-to person isn't there. Because once you stop waiting for permission, you might find out you didn't need it in the first place.

But there's a flip side. With great power comes great responsibility. Once people start making decisions without the safety net, you get speed — but you also own the outcomes. The good ones and those you’d rather forget.

Catch the full episode (and subscribe to This Meeting Could’ve Been a Podcast!) on YouTube or your favorite podcast platform.