Finding Purpose in What Keeps Us Up at Night

Building a Business that Doesn’t Need You Chris | Jones | Up at Night

What does it take to build a business that can eventually run without you?

In this episode of Up At Night, Jeremiah Curvers sits down with Chris Jones, founder of Cannabis Express, to unpack how he built a 22-location retail business across Ontario and New Brunswick—inside one of Canada’s most heavily regulated industries.

Chris shares why he deliberately avoided crowded markets, choosing smaller communities where Cannabis Xpress could become the dominant local player. He breaks down the operational systems required to maintain consistency across dozens of locations, how his approach to hiring and delegation changed as the company grew, and why scaling too quickly can create unnecessary pressure on cash flow.

The conversation also explores a challenge most founders don’t anticipate: building a company that no longer depends on its founder.

With an eventual sale always part of Chris’s plan, he’s focused on documenting processes, developing trusted leaders, and creating an organization capable of operating without him at the center.

Jeremiah and Chris also discuss the realities of operating in a highly regulated industry, consolidation in Canadian cannabis retail, acquiring real estate around the business, and the personal tradeoffs that come with years of building.

In this episode:

Why Chris chose overlooked markets instead of major cities
Scaling from a handful of locations to 22 stores
Building systems and SOPs that create consistency
Knowing when to hire—and when not to
Learning to delegate as a founder
Operating under constantly evolving regulation
Why Chris buys some of the properties his stores occupy
Preparing a founder-led company for an eventual sale
The sacrifices founders make as their businesses grow
What actually keeps Chris up at night

Up At Night is a long-form conversation series hosted by Jeremiah Curvers, founder of Polysleep, exploring the decisions, tradeoffs, mistakes, and pressure behind building and scaling companies.

No hype. No surface-level business advice. Just conversations with people who’ve actually built.

Subscribe for more conversations with founders, operators, investors, and executives building consumer businesses.

Why Most AI Strategies Fail (and What Actually Works) | David Nagy | Up At Night

Why do so many AI initiatives fail—even with the right tools?

In this episode of Up at Night, Jeremiah Curvers sits down with David Nagy, Founder of eCommerce Canada and AI & Digital Transformation Advisor, to explore what it really takes to make AI work inside a business.

Drawing from more than two decades of experience building companies and advising thousands of organizations, David explains why AI isn't a strategy—it's an amplifier. Businesses that lack strong leadership, clear operating systems, and a culture of innovation often expect technology to solve problems it simply can't.

Together, they discuss why founders are rushing into AI, the dangers of chasing hype, how to build an AI-ready organization, and why the future belongs to leaders who can combine human judgment with emerging technology.

Whether you're a founder, executive, or business operator, this conversation offers a practical perspective on navigating one of the biggest technology shifts of our time.

In this episode:
Why most AI strategies fail
AI hype vs. business reality
The importance of culture over tools
How founders should think about AI adoption
Why systems and leadership matter more than software
AI, digital transformation, and the future of business
What keeps David Nagy up at night

Guest: David Nagy
Founder, eCommerce Canada | AI & Digital Transformation Advisor

Connect with David Nagy
LinkedIn: https://www.linkedin.com/in/davidnagy/

Connect with Jeremiah Curvers
LinkedIn: https://www.linkedin.com/in/jeremiahcurvers/

🎙️ About Up at Night

Up at Night is a podcast hosted by Jeremiah Curvers featuring candid conversations with founders, operators, and industry leaders about the decisions, pressures, and trade-offs behind building exceptional businesses.

Every episode goes beyond success stories to explore what truly keeps leaders up at night.

#SEO #ArtificialIntelligence #AI #BusinessStrategy #Entrepreneurship #Leadership #DigitalTransformation #Ecommerce #Founders #Podcast

What It Really Takes to Grow a Retail Brand Today | Chris Parsons | Up at Night Ep. 1

Welcome to the first episode of Up at Night—we're excited to be back.

In this episode, Jeremiah Curvers sits down with Chris Parsons, retail strategist, author of Retail Rewired, and former retail executive at Walmart, Newegg, and Home Hardware.

Together, they explore what it really takes to grow a retail brand in today's fast-changing retail landscape.

From customer experience and omnichannel retail to AI, leadership, and scaling a business, this conversation is packed with practical insights for founders, retailers, marketers, and business leaders.

In this episode, we discuss:
• How to grow a retail brand in today's economy
• Why revenue growth doesn't always mean business growth
• The biggest mistakes retailers make
• Customer experience as a competitive advantage
• AI and the future of retail
• Scaling a retail business sustainably
• Leadership lessons from 25+ years in retail
• Hyper-local marketing and modern retail strategy

Whether you're leading a retail brand, building an eCommerce business, or simply interested in the future of commerce, this episode is for you.

Read the companion blog:
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Listen on Spotify:
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🔔 Subscribe to Up at Night for conversations with founders, operators, and industry leaders about business, leadership, retail, AI, and what really keeps them up at night.

About Chris Parsons

Chris Parsons is a retail strategist with more than 25 years of experience leading digital commerce, marketing, and retail transformation. He has held leadership roles at Walmart Canada, Newegg, and Home Hardware and is the author of Retail Rewired.

Connect with Us

Website: https://up-at-night.com/

Jeremiah Curvers: https://www.linkedin.com/in/jeremiahcurvers/

Chris Parsons: https://www.linkedin.com/in/chrisaparsons/

#Retail #RetailStrategy #RetailGrowth #CustomerExperience #AI #ArtificialIntelligence #Ecommerce #Commerce #BusinessPodcast #Leadership #Omnichannel #RetailInnovation #UpAtNight #ChrisParsons #JeremiahCurvers