Dear BTF Community,
Some enduring businesses are built far from the usual centres of capital and attention. They take shape in environments where resources are constrained, execution matters and results speak louder than reputation.
That perspective came through clearly during a conversation at BTF Winnipeg with Joshua Simair, Co-Founder and former CEO of SkipTheDishes. His experience offers a grounded counterpoint to many common startup narratives and resonates deeply with business owners thinking about growth, transition and long-term value creation.
Joshua’s story is about more than just building and selling a well-known company. It’s about judgment, discipline and learning how to work with the environment around you rather than against it.
Key Takeaways for Business Owners:
- Constraints can sharpen focus and decision making when fundamentals matter.
- Capital efficiency builds discipline that compounds over time.
- Timing is a leadership decision, not just a market one.
- Exit decisions reflect people and purpose as much as price.
Enjoy,
Mark
Location As An Advantage
Joshua doesn’t describe Winnipeg as a limitation. He describes it as a proving ground.
Building a company there forces clarity early. Costs matter sooner. Talent is hired for resilience and follow through rather than polish. Progress depends on execution, not atmosphere.
That environment, he believes, shaped both the pace and the discipline behind SkipTheDishes.
“If you make it in Winnipeg, you can make it anywhere. So if you can make it here or you can survive here, I assume that everyone here is better than they think they are.”
Lower overhead and fewer distractions meant the team had to rely on fundamentals rather than shortcuts. Decisions stuck. Standards stayed high. Over time, that discipline became a strength that held up as the company scaled.
Capital As A Tool, Not A Goal
SkipTheDishes’ early years were defined by restraint. The company relied on credit cards, grants and operating revenue rather than large funding rounds.
Joshua believes this forced the team to understand the business at a granular level.
In total, SkipTheDishes raised only $1.8 million in venture capital before its sale. That constraint sharpened attention to unit economics, customer experience and operational efficiency.
For our BTF audience, it is a reminder that capital does not replace discipline.
Confronting Bias With Execution
Raising capital from Winnipeg came with challenges. Joshua recalls being dismissed by investors who could not imagine building a large technology platform outside major tech hubs, even as SkipTheDishes’ engineering team quietly grew into the hundreds.
Interestingly, he found that some American investors were more open minded than Canadian ones who carried stronger assumptions about what could and could not be built locally.
Over time, consistent execution changed the conversation and results became harder to ignore than geography.
Knowing When To Decide
One of Joshua’s most practical insights comes from experience after SkipTheDishes. His later venture, Pivot, ultimately shut down after extended challenges and more than twenty pandemic related disruptions.
“If it’s taking long, it’s probably wrong.”
The lesson is not about rushing decisions. It is about clarity.
Founders often confuse persistence with progress. Knowing when to change direction or stop altogether is part of leadership maturity.
An Exit Driven By People, Not Price
SkipTheDishes sold for more than $200 million, plus additional funding. With hindsight, Joshua acknowledges the company could have been worth significantly more had it continued independently.
“Financially, it was a horrible decision.”
But the decision was not made on financials alone. The team was exhausted. Families were growing. Capital markets were shifting. Selling allowed the mission to continue at a different scale.
For owners considering transition, it is a reminder that exits are contextual. The right outcome depends on people, purpose, and timing, not just valuation.
Perspective After Success
Joshua speaks candidly about life after the exit.
His next venture did not succeed. Momentum did not automatically carry forward.
What remained was perspective and the desire to keep building.
He reflects on the importance of designing a life and a business that fit who you are, rather than forcing yourself into a model that does not.
The lesson applies beyond entrepreneurship. Progress often comes from alignment, not imitation.
A Lasting Impact
SkipTheDishes’ influence extends beyond its sale. At its peak, the company employed thousands and helped seed the next generation of founders and operators who continue to build in Winnipeg and beyond.
Joshua’s story is a reminder that strong businesses are not defined by location or attention. They are built through discipline, judgment and an ability to turn constraints into strength.
For those looking to hear more conversations like this, join us in Alberta for the first BTF of 2026, where more founders will share real experiences about growth, transition, and what comes after the exit.