BREAKING■ West Point grad & Army Chinook pilot turned venture analyst■ RSCM: 2,000+ pre-seed investments since 2012■ Penny Project: $4,800+ raised for charity, one coin at a time■ Author | Keynote Speaker | Ultra-marathoner | Flying trapeze■ Clients: Disney, Cisco, Adobe, P&G, Honda, FDA, The World Bank■ BREAKING■ West Point grad & Army Chinook pilot turned venture analyst■ RSCM: 2,000+ pre-seed investments since 2012■ Penny Project: $4,800+ raised for charity, one coin at a time■ Author | Keynote Speaker | Ultra-marathoner | Flying trapeze■ Clients: Disney, Cisco, Adobe, P&G, Honda, FDA, The World Bank■

YesPress Profile — San Francisco, CA

Leslie
Riley

"She flew Chinooks over Kosovo, coached Disney, counted pennies for charity,
and now she's calling your startup's number." - YesPress

Analyst at Right Side Capital Management. West Point graduate. Army Chinook pilot. Fortune 500 facilitator. Published author. Ultra-marathoner. The most interesting person in pre-seed venture you haven't heard of yet.

RSCM Analyst West Point '97 Army Aviation Author Keynote Speaker Ultra-Marathoner
Leslie Riley - Analyst at Right Side Capital Management
Analyst • RSCM • SF, CA
7
Years flying CH-47D Chinooks in the U.S. Army
2,000+
Pre-seed investments RSCM has made since 2012
$4,800+
Raised for charity through The Penny Project
20+
Years training, facilitating & coaching teams globally

Who She Is

The Analyst Who Defies the VC Archetype

Leslie Riley showed up to Right Side Capital Management carrying a resume that doesn't look like anyone else's in the room. No Goldman pedigree. No Stanford MBA. What she has is something harder to manufacture: a decade of military aviation, another decade coaching rooms full of senior executives at companies like Disney and Cisco, and a deeply human instinct for what makes teams - and founders - actually work.

At RSCM, she sits inside one of the most prolific pre-seed investment operations in the world. The firm has placed bets on over 2,000 early-stage startups since 2012 - moving fast, using data, and getting in before the professional VC world shows up with a term sheet. Leslie's job is to help figure out which of these bets are worth making.

The background that seems wildly off-script turns out to be exactly right. Pre-seed investing is fundamentally a people game. You're not reading five years of audited financials - you're reading a founder. You're asking: does this person solve problems under pressure? Do they build trust fast? Can they hold a room? Those are questions a woman who flew Chinooks over Kosovo and spent two decades helping teams unlock their own potential knows how to answer.

Leslie earned her Portuguese degree at West Point, flew helicopters in South Korea and Kosovo, navigated the often bewildering transition from military to civilian life, built a facilitation business with a client list that spans the Fortune 500 and the federal government, wrote a book on small-coin philosophy, ran ultras, trained on a flying trapeze, and landed in San Francisco venture capital. She is, as she once put it, a non-linear person.

That's not a liability. At Right Side Capital, it reads like a feature.

At a Glance

  • Analyst, Right Side Capital Management
  • West Point graduate, class of 1997
  • B.S. Portuguese Language & Literature
  • 7 years U.S. Army Aviation officer
  • Flew CH-47D Chinooks, Kosovo & S. Korea tours
  • Founder, Full Circle Inspiration
  • Founder, Lead Like a Girl community
  • Author: "Penny Perspectives"
  • Keynote speaker & certified facilitator
  • Ultra-marathon runner
  • Trained on flying trapeze

Let Go of Happily Ever After & Invest in Happily Ever NOW!

- Title of Leslie Riley's book, "Penny Perspectives" - and her philosophy on life

Origin Story

She Was Learning Portuguese at West Point While Most People Were Still Figuring Out High School

The year is 1993. Leslie Riley walks through the gates of the United States Military Academy at West Point. She picks Portuguese as her major - not the most obvious choice at a military academy, but consistent with what becomes a signature: lean into the unexpected. A summer program in Brazil arrives, and it sparks something that never quite goes away: a pull toward movement, toward unfamiliar places, toward the kind of human contact you can only have when you're a stranger somewhere new.

She graduates in 1997 and takes her commission as a second lieutenant in the U.S. Army. For the next seven years, she flies CH-47D Chinook helicopters - the heavy-lift giants of Army aviation. Tours in Kosovo and South Korea. She is one of the people in the cockpit when things need moving and the stakes are real.

Seven years in, she gets out. The transition from military to civilian life is notoriously brutal - structure collapses overnight, identity goes with it. Riley doesn't disappear into the gap. She experiments. Sales. Project management. Professional organizing. TV news production. She's taking the measure of the civilian world, finding out which skills transfer and which don't.

Career Timeline

1993 - 1997
U.S. Military Academy at West Point. B.S. Portuguese Language & Literature. Summer program in Brazil changes her relationship with travel forever.
1997 - 2004
Commissioned as 2nd Lieutenant, U.S. Army. Seven years flying CH-47D Chinook helicopters. Tours in Kosovo and South Korea.
2004 - 2010
Civilian reinvention: sales, project management, professional organizing, TV news production. Finding the shape of a second career.
2010 - 2020
Founded Full Circle Inspiration. Facilitator, trainer, and coach for Agile Coaching Institute, Leadership Strategies, and Mortgage Bankers Association.
2015
Launched Lead Like a Girl, an online community and events platform for women in leadership.
2016
Published "Penny Perspectives: Let Go of Happily Ever After & Invest in Happily Ever NOW!" - the Penny Project becomes a book.
2020s
Joined Firefly Inclusion Solutions as facilitator and keynote speaker. Clients include Disney, Cisco, Adobe, P&G, Honda, FDA, The World Bank.
2023 - Present
Analyst at Right Side Capital Management, San Francisco. Bringing 20+ years of human insight to the pre-VC investment world.

The Facilitator Years

When Disney, Cisco, and the FDA All Have the Same Problem - They Call the Same Person

What Leslie Riley found, in the years after the Army, was that teams everywhere have a version of the same problem. They stop talking. They stop trusting. They stop using what they actually know. The hierarchy calcifies. The information flows poorly. The brilliant people in the room go quiet.

She built a practice around fixing that. Full Circle Inspiration became the vehicle. The client list that followed is a masterclass in institutional variety: Visa, Disney, Capital One, Procter & Gamble, Adobe, Fidelity, The World Bank, Honda, Cisco. Federal agencies: FDA, GSA, VA. And West Point itself, the place that made her, eventually bringing her back to work with its leadership.

The methodology stayed consistent even as the clients diversified. Improve communication. Create psychological safety. Help people use their own intelligence. Get the group thinking together instead of performing separately. Riley describes the work as helping organizations "look for new perspectives when the ones they're stuck in just aren't working anymore." Which sounds simple. The rooms full of senior executives who didn't believe it when they walked in and did by the time they walked out would disagree.

She also became a keynote speaker - a TEDx talk followed, cementing a reputation as someone who could take a complicated idea about human dynamics and make it feel obvious to a room full of strangers. The skills transferable to any industry. As it turned out, including venture capital.

Notable Clients

Disney Cisco Adobe Visa Capital One P&G Fidelity Honda World Bank FDA GSA VA West Point ASAE NAHB ACS ASHA
Fortune 500 Clients8+
Federal Agencies4+
Years Experience20+
Industries Served10+

The Penny Project

It started with found money. A penny on the sidewalk. Another in a parking lot. Leslie Riley began collecting them, documenting them, and pooling the small coins into something bigger. The Penny Project became a community - dozens of people finding pennies together, tracking them, and funneling the cumulative donations toward local organizations, national charities, and individuals doing quietly extraordinary things.

The book followed. "Penny Perspectives: Let Go of Happily Ever After & Invest in Happily Ever NOW!" is ostensibly about coins. It's actually about attention - the practice of noticing small things that compound into something significant. Which, as it happens, is also what good investors do.

$4,800+ raised and counting

Lead Like a Girl

She Built a Community for Women Leaders Before "Women in Tech" Was a Conference Track

Lead Like a Girl began as a set of events and grew into an online community. The premise: women in leadership have a specific set of challenges that generic leadership training doesn't address. The solution is to create spaces where those challenges can be named, examined, and worked through - together, with other women who understand the context.

Riley brought to the community everything she'd learned across her careers. The directness of a military officer. The empathy of a trained facilitator. The lived experience of someone who spent decades navigating institutions built by and for other people. Lead Like a Girl is her thesis in community form: you don't need another credential before you start. You're ready now.

Right Side Capital Management

The Pre-VC Firm That Treats Itself Like a Startup

Right Side Capital Management

Quantitative, data-driven pre-VC investing in capital-efficient tech companies. Founded 2012. 2,000+ investments. The first institutional check for hundreds of startups.

Founded 2012
Headquarters San Francisco, CA
Check Size $50K - $300K
Stage Pre-VC / Pre-Seed
Portfolio 2,000+ companies
Focus Revenue-generating tech

Right Side Capital Management operates in the gap most institutional investors leave empty. Companies raising under $500K, too small for Sand Hill Road, too early for most angels - RSCM is often the first serious money in the room. They move fast (yes or no in roughly a week), rely on quantitative data rather than pattern-matching on founder pedigree, and have built a portfolio that now exceeds 2,000 investments.

The firm's founders - Kevin Dick, Dave Lambert, and Jeff Pomeranz - have each run startups themselves. That shapes the culture: RSCM thinks of itself as an operating company whose business model is funding other operating companies. Not a fund manager making quarterly LP calls. A team with skin in the game at the earliest possible moment.

For Leslie Riley, it's an environment that rewards her particular skillset. The human dynamics skills she's been building for decades become a lens for evaluating founders. The military background - where you learn to make high-stakes decisions with incomplete information under time pressure - maps directly onto early-stage investing. The coaching instinct means she's not just analyzing companies; she's genuinely curious about the people building them.

She brings something the spreadsheet can't capture: the ability to walk into a room with a founder and know, pretty quickly, whether they can handle what's coming.

Key Achievements

The Portfolio of a Non-Linear Career

✈

Army Aviation Officer

Seven years flying CH-47D Chinook helicopters. Deployments to Kosovo and South Korea. The skills: composure under pressure, mission orientation, team trust in high-stakes environments.

🎓

West Point Graduate

B.S. Portuguese Language & Literature, class of 1997. A summer in Brazil embedded a love of international travel and cross-cultural dynamics that has shaped everything since.

💬

Keynote Speaker & TEDx

Facilitated workshops and keynoted for Fortune 500 companies and federal agencies globally. A TEDx talk validated her voice on team communication and authentic leadership.

📚

Published Author

"Penny Perspectives: Let Go of Happily Ever After & Invest in Happily Ever NOW!" - a book about attention, small moments, and the compound value of noticing what others walk past.

🍀

Founder, Full Circle Inspiration

Built a facilitation and training business serving Disney, Cisco, Adobe, Visa, Capital One, P&G, Honda, and the FDA - a client roster that reads like a corporate hall of fame.

🏃

Ultra-Marathon Runner

Not a jogger. An ultra-marathoner. Also trained on a flying trapeze. The pattern: if it sounds uncomfortable and hard, she'll try it. This is consistent with every career choice she's made.

If there's some kind of challenge most people don't want to tackle - she'll give it a try.

- Leslie Riley, as described to World Footprints

Fun & Telling Facts

Details That Tell the Story

The CH-47D Chinook she flew has a maximum cargo capacity of 26,000 lbs. It is not a subtle helicopter.

She studied Portuguese at West Point - including a summer program in Brazil - because she is constitutionally incapable of taking the obvious path.

RSCM has backed over 2,000 startups since 2012. That's more companies than most VC firms have ever met.

The Penny Project has raised $4,800+ for charity. Found on sidewalks, parking lots, and the occasional couch cushion.

She has facilitated workshops for the FDA and West Point - possibly the two most bureaucratically serious clients imaginable - and still made them useful.

Ultra-marathon running and flying trapeze training are not hobbies she chose because they're relaxing. They are chosen because they are hard.

Her client list spans defense, tech, pharma, finance, and automotive. If you have a broken team, she's probably seen a version of your problem before.

Lead Like a Girl launched before "women in tech" became a conference industry. It was a community before communities were content.

Further Reading & Profiles
📈
RSCM Team Page
rightsidecapital.com
 🔗
LinkedIn Profile
linkedin.com
 🆘
Full Circle Inspiration
fullcircleinspiration.com
 🌟
Lead Like a Girl
leadlikeagirl.com
 🔥
Firefly Inclusion Solutions
fireflyinclusion.com
 🌎
World Footprints Profile
worldfootprints.com
 📷
TEDx Speaker Interview
womeninresearch.org
 📊
Right Side Capital Management
rightsidecapital.com