What Is It About Second-Time Founders?

Season Premiere: FutureMoney, creating generational wealth for your kids

Some founders are easier to love.

From the moment you lay eyes on them you can’t help but see dollar signs. I’m talking of course about second-time founders.

A lay up, slam dunk, grand slam… whatever your favorite sports metaphor, second-time founders sweep the fundraising floor.

But besides the benefit of experience, what is it about second-time founders that makes them sound like such an attractive investment?

Meet Philip Barrar, the founder of FutureMoney.

🎥 Watch Phil’s pitch on YouTube or listen in your favorite podcast app 🎧

Not only is he a second-time founder, Phil’s first company was a successful one.

Phil previously sold Moka, the third largest round up to invest platform for $65 million in 2021. Way to go Phil!

Except Phil didn’t really want to sell.

According to him, the board voted to sell Moka even though Phil had aspirations to build a billion dollar company.

Now, three years later, Phil is taking another crack at consumer fintech. This time it’s an investing platform for parents to build generational wealth for their kids via the Junior Roth IRA™ (more on that later).

So what makes Phil’s or any second-time founder’s pitch so much better? 

In the FutureMoney pitch, the first thing you’ll notice about Phil, is the way he carries himself. Phil’s demeanor is quiet, soft. Unassuming even. His personality doesn’t scream,

HEY I’M A SUCCESSFUL FOUNDER!

Naw… Phil’s just there, sitting across from five VCs, speaking with a quiet confidence that’s hard to miss.

It’s a confidence that whispers,

hey, I’m building something cool. you can join me if you want. if not, that’s cool too. either way, I’m going to build this company.

Despite the chill vibes, Phil has ALL the answers. And the one time he didn’t have an answer, Phil goes: 

“That's a great question. I don't think we have enough information today to be able to determine what that looks like.”

He doesn’t hesitate, doesn’t try to come up with an answer, he just admits they don’t have enough information yet to answer the question.

We. Don’t. Know. Yet.

I don’t think I can overstate how powerful this phrase can be. Admitting you don’t know something is one of the most effective ways to establish trust. Admitting when you DON’T know something, lends credence to all the answers you do have.

We’ve seen this trait before in second-time founders. While first time founders often try to compensate for their lack of experience by projecting confidence and conviction in what they are building, second-time founders have learned that knowing when you’re wrong and pivoting quickly is way more important than being right.

One more thing

This blew me away… after Phil admits he doesn’t have the answer, he continues:

“I'll mention my philosophy when it comes to building businesses. Build a business you want to own and so will others. So if you focus on good growth, cash flow, profitability, you could spin off cash dividends, you could be acquired, you could go public. There will be exit ramps every single step of the way. We know that there'll be interest from the incumbents. There's probably an opportunity to disrupt the incumbents. Too early to tell, but we have lots of great options, and I think we're building in the right way to get there.”

Quick someone write that down. That’s pitch gold right there. 🤌

Anyway… these are just my thoughts after listening to Phil’s pitch about a kajillion times while making this episode.

You can listen/watch Phil’s pitch on thepitch.show and form your own opinion. 

If you have a theory on what makes a second-time founder’s pitch sound different, I’d love to hear it. 

Now about that Junior Roth IRA™

Yes, the Junior Roth IRA™ is a trademarked name. And FutureMoney owns it. How Phil pulled that off I’m not entirely sure but the JR Roth IRA™ is a brand new financial product that wasn’t even possible nine months ago.

On January 1st of this year, the Secure Act 2.0 went into effect in the US.

This new legislation enables an existing college savings account, or 529 account, to rollover $7,000 a year into a Roth IRA after a student reaches the age of 18.

If you think this sounds complicated, you’re right. You can only transfer $7k a year, the 529 account needs to have been in existence for 15 years etc etc.

FutureMoney aims to automate the complicated parts of the rollover so that you can focus on the important part: making modest deposits for your kids today, so they can reap the benefits of time and compound money, tomorrow.

Money in the future? Why yes, thank you very much.