Inside Bobby Pinero's Journey to a $16M Series A + Fundraising Fieldnotes 1.16.24

From Calendar Density to his 'Hell Yes' moment, discover how Bobby landed a huge win for Equals

Author

Jason Yeh
January 16, 2024

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ā€¦ and now on to this weekā€™s post

I'm back with another episode breakdown from my podcast Funded - How They Raised Millions. I could talk about fundraising forever, but one of my favorite ways is to share real founder stories that illustrate the concepts I cover in this newsletter, my fundraising bootcamp, and on my socials.

This week I get to share some of my favorite takeaways from my most recent episode with Bobby Pinero, Co-founder & CEO of Equals, where he talks about closing a $16M Series A from one of the best firms in the game - Andreessen Horowitz.

Let's get into it.

Following the "Hell Yes" Path to Entrepreneurship

"I just remember having thinking through ā€œAm I ready to do this first finance hire thing again?ā€ And there was just this instinctual kind of ā€œYes, I could do it, it'd be interesting.ā€ But it wasn't that ā€œHell yes!ā€ It wasn't that energy just running through me. And then when it was, ā€œHey, let's go start Equals,ā€ all my energy came back. It was all this excitement, hell yes, absolutely. And that was the moment for me- ā€œOkay, that's it, that's the path."

Ah, the good old "hell yes" feeling every entrepreneur lives for. Yet, so many entrepreneurs I see today settle for "yes" or "sure, that might be fun."

Let me remind you once more: if it isn't a hell yes, stop and reevaluate your business immediately. If there's one thing VCs are good at, it's smelling bullshit. A VCā€™s main purpose is to figure out if the founder is all talk, or if they're actually going to lay everything down for their company.

If you don't get a rush of energy and or an overwhelming feeling of excitement when you think about your company, VCs will feel that and you're going to have a difficult time raising money.

The takeaway? Trust your instincts. Pursue endeavors that ignite your passion and enthusiasm, because those are the ones that often lead to the most fulfilling and successful ventures.

We All Question Ourselves Sometimes

"One of the things I worked on a lot by myself is just feeling like I belongā€¦ [reminding myself] of all the things that I've achieved and the things that I've worked towards are things that I'm worthy of... When I raised the last round with Andreessen, one of the scariest moments of it was going into that partner pitch of it, and I remember days before, I was like, ā€œShould I be here?"

I give credit to Bobby for being so open about what was going on in his brain as he was raising because I guarantee it's something every founder has felt at least once. From the outside looking in you might think "What? That doesn't make sense. He closed a multi-million dollar round with one of the top firms in the game." And to that, I'd say that's exactly why he felt the way he did. A lot of people think we're most scared of failure, but Iā€™d say a lot of us are actually most scared of succeeding and bracing ourselves for all the great unknowns to come.

The takeaway? It's normal to doubt yourself sometimes, but don't let it hold you back.

Calendar Density is Key

"The hard part about raising money is it's like, talk to everyone at the same time as fast as you possibly can and keep them on the same timeline as much as possible. Which means you don't sleep a lot and it's crazy and you're taking a lot of meetings and it's all night, all day. But that's the most effective way to do it."

When Bobby started sharing about calendar density- it was music to my ears. And before you say anything, I know calendar density is an extremely hard thing to execute when the market isn't doing too hot. Even when the market is booming it's hard to execute, but it's still worth it to give it a shot. There is no "half-assing" calendar density. Either you go all in or you might as well not even try.

The reason I am so huge on cramming investors into the same timeline is the same reason people run bidding wars the way they do: when people know others are interested, it makes them more interested.

The takeaway? If you're going to go for calendar density, get ready to sacrifice sleep and embrace the chaos. It might be the very thing that closes your round. It was for Bobby.

Be chased,
Jason

Listen to the full episode here:
Bobby Pinero
Equals

*If you have any suggestions on who we should interview or what we should cover in any of our shows this season, please reply and let us know!

And finally, we'd love to see you subscribe and leave a review wherever you listen to podcasts.

Thanks and happy listening!

I have to remind myself of this with marketing a ton. Can't help but feel weird repeating messages...

Doesn't have to be this exact wording and it doesn't have to be at the very beginning of your pitch....but if you find your version of this and are able to share it in a pitch, you'll do well.

When melatonin just doesnā€™t get the job done

Small asks!

If you thought this was helpful or enjoyable in any way, Iā€™d love for you to:

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  • Are you planning to fundraise? JoinĀ Fundraise with Confidence - the fundraising accelerator program that's helped founders raise over $250M šŸ’°

  • Listen with a friend to Funded, my podcast that tells the rollercoaster stories of how founders raised millions (and subscribešŸ™)

  • Ask me your fundraising questions so I can help you and cover them in a future issue

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