One of the best feelings in the world as an entrepreneur has to be failing at something (stay with me), getting back up, trying again and succeeding the second time around. There's really nothing quite like it.

in this week’s newsletter I'm going to be sharing my top 3 takeaways from my  conversation with Stacy Edgar, co-founder & CEO of Ventuer. Someone who did indeed decide to get back up and try again after an unsuccessful raise back in the fall of 2022.

Let's just say things worked out better for her the second time around...

1. Calendar Density FTW!

"We talked to close to a hundred firms in April and we finally ran the process. You know you read about it, but pulling it off is different . . . putting it all in a two-week period . . . having your data room ready to go on day one, having the follow-up materials ready to go, having your customer references there. So we talked to about a hundred and actually the raise was done by the end of April and we were over oversubscribed."

What a feeling! Stacy wrapped up her seed round in under a month in April of 2023... not one of the best times to raise. I say this to remind you that calendar density IS still possible.

I've had quite a few founders reach out to me lately about calendar density and how they no longer think it's possible during this market. My pushback is that if you reach out to 100+ investors and you aren't able to concentrate at least some momentum into two weeks, there might be a bigger problem at hand.

That all said... the truth is that Stacy didn't actually start and finish her raise in a month. I mean she did, but there is more backstory to it. Stacy had tried to go out and raise in the fall of 2022 and it didn't work out. So, when she launched her raise in the spring, she already had some of the materials prepped and was able to loop back around to a bunch of investors that had previously turned her down, showing them new traction and progress in the company.

That was my long way of saying that sometimes good things take time, and sometimes your "failures" push you to your wins.

2. A fundraise is not done until the money is IN the bank

"I think something we have come to appreciate about fundraising is, it's not done till it's done till it's like. . . DONE, right? So, we had made that mistake previously and we were [like], ‘never again.’"

Just last week, I had a founder hit me up excited about how his raise was going so far. He said he had interest from multiple investors, and he was thinking he was going to receive a term sheet. He was super pumped.

I let him know that it sounded great... but to not get too excited or create too many expectations. Things can change FAST in VC. If you recall the episode I had with Tiffany Kelly, Founder and CEO of Curastory, she had a term sheet from a firm and they pulled out.

I say this not to scare you, but to remind you to maintain that calm confidence even when things look like they might come to a close. It''s not over until that $$$ is in the bank.

3. Investor-founder relationships are a two-way street

"You don't really want somebody who's wishy-washy on your cap table. You want a hell yes, and if you're not a hell yes, like, we shouldn't be working together. So that's where I don't feel any regret. I think that it means that we're not on the same page, and if we're not on the same page, then let's give it more time or . . . it just wasn't meant to be."

This response came after I asked Stacy about some of her worst fundraising experiences. I wanted to highlight this because I think founders (especially early-stage) tend to overlook the fact that investors aren't just choosing you, you are also choosing them.

If you truly understand this, the power dynamic will no longer be you the founder asking for money, but instead it will feel more like an equal relationship. You will be asking, "does this work for both of us?".

Would you commit to dating someone you didn't know much about? Probably not. Be cautious, that's all.

Alright, those are my 3 takeaways. This doesn't even scratch the surface of the full episode so I do hope you give it a listen.

If you want to hear:

• Stacy's experience going out to raise after Techstars
• How Ventuer raised their $7.7M seed round
• How they were able to close their seed round in under a month

and more... make sure to listen to the full episode. I'll leave the links below!

Be chased,
Jason