BREAKING
Austin, Texas • Sales Renegade

Scott Leese

"The guy who sold his first deal at 27, fresh out of a hospital bed - and hasn't stopped closing since."

Six startups scaled. Nine surgeries survived. One opioid addiction beaten cold turkey. Three bestselling books. And a sales conference he invented on a Costa Rica beach, tequila in hand. Scott Leese doesn't just teach sales - he lived the hardest version of the lesson first.

6x Sales Leader 5x Founder 3x Author Fractional CRO Angel Investor
Scott Leese - Sales leader, author, and founder
160+
Companies
Scaled
6x Startups Scaled to $25M ARR
9 Surgeries Survived
15 Exits as Operator/Advisor
12 Unicorns in Portfolio
127K+ LinkedIn Followers
Origin Story

The Hospital Bed
That Built an Empire

At 23, Scott Leese was healthy, athletic - a two-sport college athlete on scholarship at Dominican University of California, playing soccer and tennis, studying psychology. Then, in the span of two days, everything changed. He was hospitalized with severe ulcerative colitis and an autoimmune disease that doctors couldn't get ahead of fast enough.

What followed was four years of hospitals, operations, and pharmaceutical dependency. Nine surgeries total - four of them major abdominal procedures. Two were life-saving. He came out the other side with no large intestine and a serious opioid addiction that had developed under medical supervision. His exit from that addiction was characteristically blunt: cold turkey, against direct medical advice.

He didn't enter sales until he was 27. No background, no training, $30K starting salary at a Bay Area startup. Just a person who had learned, the hardest possible way, that time is finite and pain has to be confronted before anything else can move. That insight became the backbone of everything he'd teach later.

The parallel he drew - between a patient admitting they have a problem before recovery can begin, and a prospect admitting their pain before they'll buy anything - wasn't a clever metaphor. It was lived experience. His first book, Addicted to the Process, made that case with enough clarity that Jeffrey Gitomer endorsed it and it hit #1 on Amazon.

Within a decade of that first $30K sales job, he had scaled six consecutive early-stage startups to $25M+ ARR, each in under three years. One got acquired for $175 million. Another became a unicorn. He'd built a consulting practice that worked with 160+ companies, co-founded a surf retreat in Costa Rica, launched the world's largest virtual sales happy hour, and started writing checks into AI companies alongside OpenAI and Anthropic.

He does all of this from Austin, Texas, with his wife Janet, their two sons Brayden and Caleb, and two dogs named Loki and Mia. He listens to music all day long. He has no large intestine. He surfs when he can. He still plays soccer.

"I learned very early in life that you have to make every minute count."
- Scott Leese
9 Surgeries before age 27

Including a total colectomy. He quit opioids cold turkey, against doctor's orders, and walked into his first sales job with zero background and no large intestine. The hospital experience directly shaped his entire sales philosophy.

The Scoreboard

160+ Companies Consulted
$175M GoDaddy/Main Street Hub Exit
650% Revenue Growth at OutboundEngine
3x AA-ISP Top 25 Most Influential

Six Startups. Six Wins.

~2007
First sales job at age 27 - $30K salary, Bay Area startup. Zero prior sales experience. Recovery from nine surgeries complete.
2011-2013
VP Sales, Main Street Hub. Grew team from 2 to 200 reps. Built offices in Austin, SF, NYC, LA. Company made Inc. 5000 twice. Later acquired by GoDaddy for $175M.
2013-2015
SVP Sales, OutboundEngine. Drove 650% revenue growth. Inc. 5000 #136 in 2015, #95 in 2016.
2016
Founded Scott Leese Consulting. Joined Qualia as SVP Sales. Published Addicted to the Process.
2016-2019
SVP Sales, Qualia. Scaled from $0 to ~15% market share. Grew headcount from 25 to 200+. Qualia became a unicorn.
2017
Co-founded Surf and Sales with Richard Harris and Jeff Coleman. Literally conceived on a Costa Rica beach after a surf session.
2020
Co-founded Thursday Night Sales (world's largest virtual sales happy hour) and GTM United private community.
2024
Founded Milos Ventures - angel/venture fund investing in AI, robotics, defense, energy, cleantech. Portfolio: OpenAI, Anthropic, Groq, Scale AI, Perplexity.
2016 - Present
Scott Leese Consulting
CEO & Founder
Fractional CRO and GTM advisor. 160+ companies from $0 to $25M ARR. Specializes in early-stage SaaS sales architecture.
2017 - Present
Surf and Sales
Co-Founder
Annual summit in Playa Grande, Costa Rica. Sales coaching plus actual surfing. The premise: the best deals get done in the in-between moments.
2020 - Present
Thursday Night Sales
Co-Founder
The world's largest virtual sales happy hour. Thousands of sales pros. Weekly. Free. Built because existing communities weren't serving practitioners.
2024 - Present
Milos Ventures
Founder
Venture and angel investing. AI, robotics, defense, cleantech. Co-led with Taylor Leese. AngelList syndicate open to LPs.
Published Works

Three Books. One Lived Philosophy.

2017
Addicted to the Process
How to Close Transactional Sales with Confidence and Consistency
The book that made his name. Draws a direct line between addiction recovery and the sales process - a prospect must admit and confront their pain before they'll act, just like an addict must confront their problem before recovery begins. Endorsed by sales legend Jeffrey Gitomer.
Amazon #1 Bestseller
2021
More Than a Number
The Modern VP Sales Playbook
Written for sales directors preparing to step up, sitting VPs looking to sharpen their edge, and founders who want to actually empower their sales leadership. Treats the VP role as a distinct craft, not just a promotion from rep.
2021
From Rep to Manager
A Step by Step Guide for Taking the Leap into Sales Leadership
Co-authored with Ryan Walker. Covers the full arc of the IC-to-manager transition: how to evaluate the opportunity, how to interview, what to do in your first 30-60-90 days when everyone is watching. Practical, not theoretical.

Learned, Earned, Burned

Before leaving any role, Scott runs every decision through this three-part filter. It's the most honest career framework in sales - and it came from watching too many people leave too early or stay too long.

01
Learned
Have you maxed out what this role can teach you? If you're still growing, still facing new problems - that's value you'd be walking away from. Skills compound. Don't leave them on the table.
02
Earned
Have you gotten the financial upside you signed up for? Equity vesting, bonuses tied to milestones, a raise you've been earning toward - leaving early means leaving money behind. Be honest about that math.
03
Burned
How depleted are you? Burnout isn't a badge. It's a cost. If you've learned everything and cashed out but you're running on empty, that's the signal. Protecting your mental health is not a soft priority - it's an operational one.

Surf and Sales: Where Tequila Met Strategy

The story of Surf and Sales begins exactly the way you'd want it to: two sales guys, a Costa Rican beach, the sun going down, and a drink in hand after an evening surf session. Scott Leese and Richard Harris looked at each other and said, essentially, why don't the sales conferences we go to feel anything like this?

The insight wasn't about surfing. It was about the in-between moments. The conversations that happen not on stage but in the water, at dinner, walking back from the beach. Traditional conferences pack schedules so tight there's no room for the actual relationship-building that makes careers. So they built a different thing entirely.

The Surf and Sales Summit runs annually in Playa Grande, Costa Rica. No experience required for the surfing - they provide lessons. The sales coaching is real, the speakers are practitioners not theorists, and the format is deliberately loose enough to create space for the conversations that actually matter.

  • Co-founded with Richard Harris and Jeff Coleman in 2017
  • Annual summit format: one week, Playa Grande, Costa Rica
  • Mix of surf lessons, sales workshops, and unstructured time
  • Named Best Sales Podcast for the accompanying show
  • Built on the philosophy that real relationships need breathing room
Origin Story

The Beach That Started It All

Scott and Richard Harris were sitting on a beach in Costa Rica with tequila after an evening surf session when they decided to build their own conference. The existing ones weren't working. Too formal. Too scripted. Not enough actual human connection. They wanted to build something where the strongest bonds happened between the sessions - in the water, at dinner, on the walk back from the beach.

Core Philosophy
"The strongest relationships are built during the 'in-between' moments."
- Scott Leese, Surf and Sales Co-Founder
In His Own Words

Unfiltered. No Filler.

"Success boils down to one question: 'How bad do you want to make it happen?'"
Addicted to the Process, 2017
"I don't really believe anybody cares that much about their job or hitting quota. They care about what those things can do for them or their family or their loved ones."
On motivation in sales
"If you were to leave today to go to some other place, and you don't have people that would follow you, you're not doing your job right."
On sales leadership
"The big win to me is going in, taking this complicated idea and finding a way to simplify, simplify, simplify the messaging."
On GTM strategy
"You can control your efforts and that oftentimes is the differentiator between who does well and who doesn't."
On consistency
"Anyone that tells you they have it nailed is flat out lying - a sales rep is one of the most difficult hires you can make."
On hiring in sales
What's Next

Milos Ventures: Betting on What's Coming

In 2024, Scott formalized what he'd been doing informally for years - backing early-stage companies at the frontier. Milos Ventures, co-led with Taylor Leese (who had already made 40+ startup investments), focuses on the sectors that will define the next decade: AI, robotics, defense, energy, and cleantech.

The portfolio reads like a who's-who of the AI moment: OpenAI, Anthropic, Groq, Scale AI, Perplexity AI, Lambda, Rescale, and Thinking Machines Lab. These aren't passive bets - they're the companies Leese studies, talks about publicly, and integrates into his GTM advisory work.

After 15+ exits as an operator and advisor, including a unicorn and a $175M acquisition, the move into investing is less a career pivot than a natural extension. He understands how companies go from zero to revenue. Now he's writing checks to help the next generation do it faster.

OpenAI Anthropic Groq Scale AI Perplexity AI Robotics Defense Cleantech
Investment Focus Areas
  • Artificial Intelligence & Foundation Models Active
  • Robotics & Automation Active
  • Defense Technology Active
  • Energy & Cleantech Active
  • B2B SaaS GTM Tools Selective
AngelList Syndicate
Milos Ventures runs an open syndicate on AngelList. Co-investors can access deal flow in AI, robotics, and deep tech alongside the fund.
View Syndicate

Things You Didn't Google

🎓
Two-sport college athlete at Dominican University of California on an athletic scholarship - soccer and tennis simultaneously, earning All-Conference honors in soccer while studying Psychology and Religious Studies.
🏥
Has physically no large intestine after a total colectomy performed during his twenties. He discusses this openly. His first book's core metaphor came directly from the experience of addiction and recovery.
🤝
First sales job: $30,000 a year at a Bay Area startup, age 27, with no sales background whatsoever. That's the entire origin story. No family connections, no MBA, no sales training program.
🌊
The Surf and Sales Summit was literally conceived on a Costa Rica beach with tequila in hand after an evening surf session with Richard Harris. That's not marketing copy. That's actually what happened.
🎵
Listens to music all day, every day, as a core productivity ritual. It's not background noise - it's deliberate. His favorite book is The 48 Laws of Power by Robert Greene.
📊
96.5 out of 100 authenticity score on Favikon - one of the highest in B2B content. Ranked #13 in U.S. Sales on LinkedIn and #30 globally. The engagement on posts about opioid addiction and mental health routinely outperforms sales content.
Copied!