AJ Smith (Outlander VC) / VC Breakdown & Contact

About AJ Smith

AJ Smith is a multi-time founder turned investor at Outlander VC who openly uses his failed job-seeker startup as part of his investing approach, and applies songwriting principles from his music career—including opening for the Eagles on violin with Glenn Frey as a mentor—to help founders craft compelling narratives that get stuck in people's heads. He's known for his headline test where he spends 90 seconds reading only slide headlines to judge if founders can compress complex engineering into simple, memorable pitches, and runs founder boxing events plus sweat equity meetups to build toughness while normalizing the reality of pitching 150+ VCs for early funding.

Where they've Worked

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Video Interview

On coaching founders to tell a better story

"I want you to take some of the biggest, most complex engineering ideas in the universe and let's get it stuck in everybody's heads in the shower. At the end of the day, life is storytelling."

AJ Smith

Partner, Outlander VC

On building thick skin for the fundraising grind

"You need to be prepared to pitch 150 VCs to get to your first check. And if you are not prepared for that, you might not be ready for this process."

AJ Smith

Partner, Outlander VC

On the pitch deck "headline test"

"If your pitch deck, I can't read it headline to headline and quickly understand exactly what your business does and why it's important and why it's consequential, then you should probably take another stab at it."

AJ Smith

Partner, Outlander VC

On building honest urgency without killing the deal

"I'm not going to do a deal with somebody who's dishonest with me. I don't mind somebody who can add an extra 15% of color to something. Because I think you need to be able to do that as a storyteller, as a founder. But if you fully misrepresent something to me, then we won't be able to work together."

AJ Smith

Partner, Outlander VC

On being transparent with your investors after closing

"Don't give us the rose colored glasses. That's for you to go on and sell to your customers and your outside world and your grandma. I want the truth because otherwise, five of the seven of us on the Outlander team have been founders. We've probably been in a similar situation and we can help you. So let us help you."

AJ Smith

Partner, Outlander VC

About their Fund

Outlander VC

Sectors

AI, Robotics, Defense, Deeptech / Hardware, Climate, Space, Transportation, SaaS

Rounds

Pre-Seed - Seed

Avg Check Size

$500k - $2.5M

Notable Investments

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Outlander VC uses intelligence-style human assessment methods developed from founder Paige Craig's Marine Corps intelligence background to evaluate founders through deep life conversations and a structured framework that scores vision, intelligence, character, and execution, rather than relying on decks or references. The firm specifically seeks oddball, unknown, under-networked, and underrepresented founders in non-core markets like the U.S. Southeast, investing from Day Zero often as the first and only check before teams even have compelling product ideas.

Other partners at the fund