Justin Strange

Vancouver, Canada

Justin
Strange

Founder  ·  Builder  ·  Creator  ·  Operator

Twenty years building businesses from first principles. Currently at the intersection of technology, human confidence, and what AI can do for the businesses most people forgot to automate.

About

The Long Game

I have been self-employed since 2004. That is not a boast. It is context. It means I have never had the option of waiting for someone to hand me a plan. Every business I have built started with a problem I could not stop thinking about and a decision to do something about it.

The Confident Man came from watching something happen in real time. A generation of young men losing their footing. Not dramatically, but quietly. Confidence eroding, relationships fracturing, the social architecture that has held communities together for generations starting to give way. Less marriage. A distorted picture of what family life looks like. A deep uncertainty about what a man is even supposed to be. I built something to address it directly.

Hollinger is the infrastructure around the things I believe are worth building. A holding company for technology and AI ventures, and a serious applied AI team. Hollinger AI builds performance systems around the work businesses already do: sales, follow-up, operations, reporting, and internal knowledge. The businesses that need AI the most are not in Silicon Valley. They are on Main Street, and most of them are still running on spreadsheets and goodwill.

Outside of work I fly, I train, I spend as much time outdoors as possible. Ideally somewhere warm, preferably somewhere new. I give back where I can. I have been a member of the Entrepreneurs' Organization and served on the Business Leaders Council advising the Premier of British Columbia on small business policy. My children are the best thing I have ever built.

Justin Strange
Justin Strange
Justin Strange

“The best businesses I have ever seen were not built on an idea. They were built on a refusal to accept the way things already were.”

Justin Strange

Portfolio

Portfolio

Live and in development across technology, hospitality, media, and AI.

HH

Holding Company

Hollinger Holdings

A holding company focused on emerging technologies and AI. Built to acquire, incubate, and operate ventures at the leading edge of what is possible.

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H·AI

Applied AI Systems

Hollinger AI

Applied AI performance systems for businesses that need serious automation, team workflows, and measurable operating leverage.

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HGO

AI · Real Estate Sales

Hugo AI

A realtor-facing AI sales and lead system built to keep follow-up moving, surface warmer conversations, and bring more personality to pipeline work.

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ORC

AI · Lead Intelligence

Orca AI

A serious real-time lead generation and intelligence system for operators who need clearer signals, faster qualification, and disciplined outreach.

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HM

Social · Media Management

Hollinger Media

A social media management platform built for businesses that take their presence seriously. Schedule, publish, and analyse across every channel from one clean dashboard.

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CM

AI · Coaching

The Confident Man

An AI-powered confidence coach for men. Built in response to a cultural shift that nobody was talking about. A generation that needed a direct answer.

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BW

Hospitality · Brand

Big Willy

A bold hospitality brand built around character, quality, and the kind of experience people talk about after. More soon.

TC

Marketing · Agency

Then Cocktails

A boutique marketing agency. Built for brands that want to stand out, not blend in. Strategic, creative, and small enough to actually care.

CRM

Technology · CRM

Crumb

A CRM built for operators who are tired of paying enterprise prices for features they do not use. Clean, fast, and built around how real businesses actually work.

HP

Energy · Technology

Hollinger Power

Intelligent power management for commercial and industrial operators. Precision infrastructure for businesses that cannot afford downtime.

CW

AI · Coaching

The Confident Woman

The female counterpart to The Confident Man. An AI coach designed for women navigating confidence, dating, and the social dynamics that nobody talks about directly.

ATS

Relationships · Media

Ask The Sexes

Relationship advice from the one perspective that actually matters. Real answers from the opposite sex, unfiltered and on demand.

WI

Travel · Lifestyle

Wander Index

A private travel intelligence platform for people who move differently. Curated itineraries, insider access, and a community that knows the difference.

BP

Health · Performance

Baseline Performance

Precision wellness for high-performers. Biometric tracking, recovery protocols, and AI-driven insights built around how serious people actually train.

CL

Finance · Tools

Clear Ledger

Financial clarity for independent operators. A smarter way to track, plan, and protect the money you built without the overhead of a family office.

OD

Productivity · AI

Operator Desk

An AI workspace built for founders and operators who run lean. Everything you need to think, plan, and execute in one clean environment.

SC

Fashion · Community

Sophia's Closet

Clothing swap built for women. A curated marketplace to trade, share, and discover wardrobe pieces without the waste of buying new.

PIQ

Real Estate · Tech

Property IQ

A smarter way to find, evaluate, and move on residential real estate. Built for the buyer who does their homework and moves fast when it counts.

RR

Communications · AI

Reply Ready

AI-powered communication tools for small business. Better customer conversations, faster response times, and the polish that makes people trust you.

SS

Operations · AI

Scale Stack

Operational infrastructure for businesses that have outgrown their original systems. Built to scale without rebuilding from scratch.

20+

Years Self-Employed

EO

Entrepreneurs' Organization Alumni

BLC

BC Business Leaders Council, Premier's Advisory

“Discipline is life's currency.”

Justin Strange

If you have something worth building, let's talk.

Whether it is an investment conversation, an AI pilot for your business, or a collaboration worth exploring. The contact form is short and I actually read it.