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Salem, Oregon  ·  Est. 2026

Hard-won insight.
Plainly delivered.
No polite fictions.

Ben Pickett brings 25 years of enterprise-scale experience to the keynote stage, the boardroom, and the market. Without the hype.

Start a Conversation → About Ben
Pickett Ventures LLC
01
Speaking & Advisory Keynotes, workshops, board advisory
02
AI & Technology Practical AI implementation for SMB & mid-market
03
Strategic Consulting Bespoke advisory for founders & executives
04
Investment Management Systematic, multi-signal approach across public markets
Accepting new engagements  ·  Salem, OR
Credentials
25+ Years Building & scaling complex systems
1,000+ Stores Retail SRE at enterprise scale
4 Platforms Speaking · AI · Consulting · Investment
Former Mayor Jefferson, Oregon · Elected 2013
Ben Pickett
Ben Pickett
Founder & Managing Member
Investment AI Strategy Operations Falconry Nike Alumni
25+Yrs Experience
1K+Stores via SRE
MayorJefferson, OR
5Keynote Topics

Founder

Two decades building.
Now charting my own.

Ben Pickett is an investor, strategist, and speaker with 25+ years of experience building and operating complex systems at scale. He has led SRE across more than 1,000 retail locations at Fortune 100 companies, co-founded an AI company, and served his community as an elected Mayor. He has led global teams, stood up multi-hundred-million-dollar programs, and spent years learning what actually separates the ideas that compound from the ones that plateau.

Pickett Ventures is the vehicle for what comes next: a fully independent, multi-platform firm operating across speaking, AI implementation, strategic consulting, and systematic investing. No external bosses. No polite fictions. Own the work.

"The best opportunities are where the crowd is wrong and you can prove it. The edge isn't philosophy; it's operational."

Outside the firm, Ben is a licensed raptor propagator (Harris Hawks and Falcon Hybrids), a photographer, and an avid outdoorsman based in Salem, Oregon, where Hunting Hawks operates as the falconry side of the operation.

Visit benpickett.com →

The Thesis

The edge is operational,
not philosophical.

01

Conviction over consensus.

The best opportunities live where the crowd is wrong and you can prove it. That takes independent thinking and the willingness to be early.

02

Asymmetry over certainty.

Find positions where the upside dramatically outweighs the downside. In trading, consulting, and client selection.

03

Precision over volume.

Fewer, better decisions, in markets and in the room. The right analysis at the right time moves more than a hundred meetings.

04

Ideas compound too.

Capital compounds. So does knowledge. The right thinking, delivered to the right room at the right time, creates lasting returns.

Four Platforms

Four platforms.
One operating thesis.

Speaking & Advisory

Five developed keynote topics at the intersection of AI, leadership, and asymmetric thinking. Available for corporate events, executive summits, and board advisory engagements. Full speaker profile at benpickett.com.

Keynotes & workshops · Contact for availability & fees

AI & Technology

Practical AI implementation for businesses that need results, not presentations. From agentic workflows and custom tooling to full deployment, targeting SMB and mid-market clients ready to move.

Project-based · No fluff, no pilot theater

Strategic Consulting

Bespoke advisory for founders, executives, and boards navigating complexity. Go-to-market strategy, operational design, and growth architecture rooted in 20+ years at Fortune 100 scale.

Project-based and retainer · Inquire for engagement terms

Investment Management

Systematic, multi-signal approach to public markets, combining quantitative research, macroeconomic positioning, and disciplined risk management.

Systematic, multi-signal · Contact for structure details

25+ Years of Experience
4 Active Platforms
1,000+ Retail Stores via SRE
0 Polite Fictions

What People Say

Heard from the
people in the room.

★★★★★

"I've worked with hundreds of enterprise executives over a 20-year career, and I can count on one hand the people who can walk into a room full of salespeople and genuinely electrify them. Ben Pickett is one of those people. He made a room full of hardened enterprise sales professionals lean forward in their seats, laugh out loud, and walk away remembering exactly why what we do matters. That speech is still talked about. Years later, people from that kickoff still bring it up. If you're looking for a keynote speaker, a thought leader, or someone to represent your brand on stage, Ben Pickett is the real thing."

Dave Best
Dave Best
Vice President, SustainableIT.org
★★★★★

"I've worked with Ben across vendor partnerships and speaking engagements for nearly a decade. When I brought him in to speak at an invitation-only DevOps workshop for CTO-level executives in Hawaii, he delivered exactly what that audience needed: no theory, no filler, just hard-earned perspective from someone who had lived it at global scale. He was the person everyone wanted to keep talking to when it was over. There is no one I would recommend more confidently for a senior technology audience."

J. Damian Vitale
J. Damian Vitale
Regional Sales Manager, Silicon Valley & Hawaii, Perforce Delphix

Ways to Work Together

Three ways to
engage Pickett Ventures.

Advisory Retainer

Monthly engagement for founders and executive teams that need a senior strategic mind on call, without a full-time hire. Bespoke scope, direct access.

Inquire →

Project Engagement

Defined-scope projects across strategy, AI implementation, and go-to-market. Clear deliverables, fixed timelines, no scope creep. Done right the first time.

Inquire →

Speaking & Keynotes

Ben speaks at executive summits, corporate events, and leadership programs on AI strategy, asymmetric thinking, and operating at scale. Five fully developed keynote topics available. See the full topic list and speaker profile at benpickett.com.

Speaker profile → Book Ben →

Writing

Perspective from
the field.

Enterprise AI, technology leadership, and the uncomfortable truths most people in this industry won't say out loud. Published on Medium.

Follow on Medium →
AI Governance Apr 11, 2026 7 min read

Anthropic's Mythos Just Proved Enterprise AI Governance Is a Cybersecurity Emergency

An AI escaped containment, found thousands of zero-day vulnerabilities autonomously, and triggered a Fed-level response. Machine speed doesn't wait for human response time. The gap between them is your problem.

Read on Medium →
AI Security Apr 1, 2026 8 min read

Anthropic's Two Leaks in Five Days: What Enterprise Security Leaders Must Do Now

The company warning the U.S. government about AI cybersecurity risks shipped a misconfigured CMS and an unstripped source map within the same week. These are not anomalies. They are a case study in the gap between AI security posture and AI security operations.

Read on Medium →
Shadow AI Mar 28, 2026 5 min read

Your Employees Are Already Using AI You've Never Approved

78% of employees use AI tools IT never sanctioned. Here's what that number actually means and why blocking it makes everything worse. The answer is not better policy enforcement. It is giving people a better option.

Read on Medium →
AI Strategy Mar 25, 2026 3 min read

AI Is an Accelerator, Not a Replacement for People

Companies augmenting human capabilities outperform those eliminating roles, and 50% of organizations making AI-driven cuts are expected to rehire by 2027. The workforce reduction narrative around AI is not just ethically fraught. It is bad strategy.

Read on Medium →

Get in Touch

Let's find the
right fit.

Whether you're looking for a strategic advisor, a speaker, or an AI implementation partner, the first conversation is always the right place to start.

pickettventures.ai
Pacific Northwest, United States
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Pickett Ventures

Hard-won insight. Plainly delivered. No polite fictions.

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© 2026 Pickett Ventures LLC

Speaking. AI. Strategy. Investing.

Nothing on this site constitutes investment advice or a solicitation to buy or sell any security. Pickett Ventures LLC is not a registered investment adviser. Past performance does not guarantee future results. All investments involve risk.